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$243

2 BR / 2 BA / Sleeps 4

1 Reviews

$243

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Cozy and clean in Gt Barrington- 1 week in summer!

Great Barrington house – 8.5 mi away
2 BR / 2 BA / Sleeps 4 | Quick view
Very Good1 Reviews

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Reviews

(1)

Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There are about twelve (12!) hiking trails in Great …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Porch
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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Reviews

(1)

Easy, comfortable summer getaway!

Left on Feb 02, 2015 for a stay in August 2013

My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cross ventilation and the screened in porch was a great place to linger over coffee in the morning. The location is also wonderful! It is only a 5 minute drive to lake Mansfield, 7or 8 …

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$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

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Field View Cottage , Convenient to All Berkshire

Great Barrington house – 5.0 mi away
4 BR / 2 BA / Sleeps 9 | Quick view
Excellent1 Reviews

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Reviews

(1)

The perfect house for friends and family to share! Bright,uncluttered, and inviting, with privacy and views just minutes to town. There are two fireplaces,a sunken living room, dining room with seating for 10, 4 bedrooms, 2 full bathrooms, and a cozy hang out area in the basement. There is a washer and dryer, …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Best Memorable Thanksgiving Ever

Left on Feb 05, 2015 for a stay in November 2014

This was the first time we had a rental cottage, but it surpassed all of our expectations. The cottage was clean and well arranged. Kitchen was spacious enough for more than a few people cook together. Fireplace was lovely and so fun! The neighborhood was so quiet and calm. It snowed right before Thanksgiving, and the view was priceless! We would like to come back again!

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$179

1 BR / 1 BA / Sleeps 3

12 Reviews

$179

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Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage – 7.9 mi away
1 BR / 1 BA / Sleeps 3 | Quick view
Excellent12 Reviews

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Reviews

(12)

Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hills and verdant meadows.. Nature lovers, artists…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Central heating
  • Parking
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly

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Reviews

(12)

Peaceful and relaxing weekend

Left on Sep 06, 2011 for a stay in August 2011

My husband and I stayed here while visiting Great Barrington for the weekend. The space is immaculate and very quaintly designed. There is ample space to spread out. Bed is comfortable, full bath is very clean and towels are provided. No stovetop, but a full fridge and kitchen sink. Not much need for a kitchen since downtown is just minutes away and offers plenty of excellent restaurants. The …

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$250

2 BR / 1 BA / Sleeps 5

2 Reviews

$250

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1940's Cabin with fantastic 180o mountain views!!

Great Barrington house – 4.7 mi away
2 BR / 1 BA / Sleeps 5 | Quick view
Excellent2 Reviews

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Reviews

(2)

Please note that this property is not winterized so it's not available this winter of 2012. I am winterizing this spring & the property will be available on a year around basis stating on 5/15/2013. Please go to (website: hidden) listing #219964 to see my reviews, I am new to flipkey. Located in South Egremont, 3 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly

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Reviews

(2)

What a wonderful cabin! What an amazing location! - The perfect log cabin getaway

Left on May 20, 2013 for a stay in May 2013

This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential cozy cabin. Jonathan's Luka Lodge has it-- you feel totally isolated and yet you're only minutes away from delicious restaurants and gourmet shopping. The furnishings and decor are subdued and add to the rustic but …

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$250

5 BR / 2 BA / Sleeps 12

13 Reviews

$250

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Berkshire Farmhouse Vacation

West Stockbridge house – 14.4 mi away
5 BR / 2 BA / Sleeps 12 | Quick view
Excellent13 Reviews

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Reviews

(13)

Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Country kitchen with dish washer, microwave, toaster …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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Reviews

(13)

Fantastic place to stay in the Berkshires

Left on Jan 08, 2014 for a stay in December 2013

Elaine was a very gracious host, and the...accommodations were lovely
and in a great location. The historic house has a lot of charm and many
nice updates, especially the clean, updated bathrooms and the huge
screened-in porch. ... We had room to spare, and everyone had a room to
themselves. The kitchen was well stocked, and the living room very cozy...
This would be a great place for skiers. …

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$125

2 BR / 1 BA / Sleeps 6

2 Reviews

$125

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Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge condo – 16.4 mi away
2 BR / 1 BA / Sleeps 6 | Quick view
Excellent2 Reviews

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Reviews

(2)

Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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Reviews

(2)

Great home, great location

Left on Nov 26, 2013 for a stay in November 2013

Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to some wonderful hikes, gorgeous villages and towns and some wonderful food options and restaurants. Already looking forward to the next visit!

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$149

1 BR / 1 BA / Sleeps 2

5 Reviews

$149

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RiverSong Suite In The Berkshires

North Egremont condo – 8.1 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent5 Reviews

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Reviews

(5)

Located in the Berkshire mountains on more than 5 acres surrounded by 29 acres of conservation land. Featuring beautiful views of meadows, mountains and farm land bordering the crystal clear Green River (great trout fishing).Only 10 minutes from Great Barrington's Main Street stores, resturaunts, theaters, and events…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(5)

Enjoyable stay

Left on Aug 23, 2013 for a stay in August 2013

My husband and I stayed 2 nights at Riversong suite - a lower level studio/suite in Barbara and Philip's house. Their property is beautiful overlooking an open field and we enjoyed sitting in the rocking chairs in the gazebo out back. We enjoyed being away from congestion in a peaceful setting. Barbara has thought of everything in terms of furnishing and decorating the space and making sure …

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$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

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Beautiful Berkshire House w/ Tennis

Sheffield house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent16 Reviews

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(16)

Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. 88 acres of land with views of Mt. Washington and Mount Everett promises privacy, …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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Reviews

(16)

home on the range

Left on Jul 08, 2010 for a stay in May 2003

my wife and i stayed at this lovely home for the entire summer, may through october, and we returned during the new year holiday the following winter. the setting is extremely private and sits on a gorgeous field surrounded on one side by the mountains and the other side of woods and cleared fields with an infinite skyscape, especially interesting on a starry night for heaven seekers.
the home …

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$325

4 BR / 3 BA / Sleeps 8

3 Reviews

$325

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Historic South Lee Schoolhouse near Stockbridge

Lee house – 13.7 mi away
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent3 Reviews

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Reviews

(3)

Enjoy all the Berkshires has to offer in our new (2014) restoration and outstanding renovation of the historic South Lee Schoolhouse. Perched on a hillside just across the road from the Housatonic River and Beartown State Forest in the hamlet of South Lee, just outside of Stockbridge, the 1892 schoolhouse has been …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

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Reviews

(3)

spacious, comfortable, and otherwise delightful

Left on Apr 13, 2015 for a stay in April 2015

Great place to stay; would be ideal for family groups or others looking for a mix of private spaces and togetherness.

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$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

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Bird Watchers Delight! Country Get-Away w/Pond!

Lee house – 18.0 mi away
5 BR / 3 BA / Sleeps 11 | Quick view
Very Good8 Reviews

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Reviews

(8)

Beautiful house surrounded by protected woodland and a small beaver pond behind your backyard. All kinds of birds and wildlife. 5 Bedrooms, 2.5 baths, brand new kitchen, open living/dining room, laundry room. Wood stove that can function as a fireplace. 3 heating zones for comfort. All new electric and plumbing in …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Central heating

Details

Reviews

(8)

Great Girlfriends' Getaway!

Left on Jan 31, 2012 for a stay in January 2012

We decided on fairly short notice to get away with a group of girlfriends to the Berkshires. Robin was so gracious to accommodate us on short notice. We arrived on a frigid day to find a clean and comfortable house, with a fire laid and ready for us. The kitchen had everything we needed for preparing our meals. We especially love the oversized coffee mugs! It's the little things that make a …

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$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

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The Smith Farm Homestead

Alford B&B – 9.9 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent3 Reviews

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Reviews

(3)

The Smith Homestead in Alford Massachusetts has been homesteaded and farmed by our family for the past two centuries. Located on one of the nicest settings in the Berkshires, with 30 acres of fields and woods, and the crystal clear Alford Brook running through, we are central to all the cultural events and outdoor …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet

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Reviews

(3)

Beautiful

Left on Apr 09, 2013 for a stay in March 2013

Five stars! Perfect location for a getaway. A quick ride into the beautiful downtown Great Barrington. I have had many good night rests in this room. The hillside view is spectacular. And the best cup of coffee around.

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$100

4 BR / 3 BA / Sleeps 15

8 Reviews

$100

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Race Mountain House

Sheffield house
4 BR / 3 BA / Sleeps 15 | Quick view
Excellent8 Reviews

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Reviews

(8)

The Race Mountain House is set high on the slopes of the Taconic Mountains in Southern Berkshire County. Large, east-facing windows look out over a sweeping view of the Housatonic River Valley. In the early hours, the house floods with warm morning light and sunrises are spectacular. The inviting, creative design …
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(8)

Perfect weekend getaway!

Left on Feb 12, 2014 for a stay in December 2013

A truly beautiful house in such a magical place! I spent a lovely weekend here with a group of friends from NYC, and we all had our own space to relax, and enjoyed coming together to cook and unwind in the spacious kitchen and living room (the fire place is awesome!). The perfect spot for a peaceful weekend in the woods, plus it's only a short walk to Race Brook Lodge to enjoy some food and …

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$143

3 BR / 3 BA / Sleeps 6

1 Reviews

$143

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Lake community - Berkshires

Sandisfield house – 16.2 mi away
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

Home on 2.5 wooded acres in a private lake community, with vacant wooded acres on both sides. Amenities of the community include non-motor boat lake, outdoor heated swimming pool, tennis courts, exercise facility, clubhouse and walking trails. The home is located in the Berkshires, a popular year round destination …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Suitable for children - ask

Details

Reviews

(1)

Great house in a beautiful lake community

Left on Feb 01, 2015 for a stay in July 2014

We stayed at this beautiful house in a lovely lake community. The house is open and bright and very comfortable. We spent most of our time on the large screened back porch, listening to the birds. It's a very short walk to the serene, non-motor boat lake and beach area. When not at the beach or heated community pool, we explored the Berkshires. There were so many things to do....Tanglewood …

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$465

4 BR / 4 BA / Sleeps 12

3 Reviews

$465

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Gem of the Berkshires, walk to downtown & lake.

Great Barrington condo – 7.3 mi away
4 BR / 4 BA / Sleeps 12 | Quick view
Excellent3 Reviews

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Reviews

(3)

This sparkling, newly renovated cottage is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions. The house has been renovated by a contemporary designer. It has an open floor plan, making each room flow into another. The main level …
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

beautiful review and wonderful owners.

Left on Jul 03, 2012 for a stay in June 2012

We stayed here for a weekend with friends and couldn't have asked for a better time. The house is located on a hill above Great Barrington and has access to a lake. Ephrat is perhaps the nicest owner I've ever worked with on a vacation rental. She treated us like guests, not renters, and took the time to give us a wonderful tour of the beautiful property. The next morning she even dropped off…

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$250

3 BR / 2 BA / Sleeps 8

2 Reviews

$250

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Berkshires Spacious Comfortable Charming Farmhouse

Lee condo – 17.5 mi away
3 BR / 2 BA / Sleeps 8 | Quick view
Very Good2 Reviews

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Reviews

(2)

Experience a little of old New England. Our vacation rental is a charming historic family farmhouse apartment with lots of room and comfort,2100Sq.ft., situated on 22 acres. Built in 1782, our farm was famous for breeding Plymouth Barred Rock chickens. In the 1800's, one of these barred rock roosters won the grand …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

lovely stay

Left on Sep 24, 2010 for a stay in August 2010

The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$300

3 BR / 2 BA / Sleeps 5

2 Reviews

$300

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Perfect Getaway for Body, Mind and Soul

Lee cottage – 16.7 mi away
3 BR / 2 BA / Sleeps 5 | Quick view
Excellent2 Reviews

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Reviews

(2)

** Rental is only available for 2 week minimum during the summer (July - August) Special Summer Deal -- Rent for the Season (July and August) and get either the last week in June OR the first week in September for half price! This adorable cottage has all the ingredients for the ultimate retreat for body, mind and …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(2)

Great getaway!

Left on Feb 12, 2012 for a stay in August 2011

We had the most amazing time. This adorable home is so close to everything and yet is feels very private and secluded. It provided a perfect balance for relaxation and adventure. One of the best parts for us was the awesome lake. We certainly hope to come back very soon!

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$199

3 BR / 2 BA / Sleeps 6

22 Reviews

$199

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The Cottage B&B near Tanglewood in The Berkshires

Stockbridge B&B – 14.6 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent22 Reviews

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Reviews

(22)

The Cottage, in picturesque Stockbridge, has the PERFECT location -- minutes from Main Street Lenox, Main Street Stockbridge, The Norman Rockwell Museum, Berkshire Botanical Gardens, Tanglewood Music Festival, The Shrine of the Divine Mercy at the Congregation of Marians, shops, theaters, hiking an biking. Private…
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(22)

Location, location, location

Left on Apr 09, 2011 for a stay in August 2006

This place is in one of the absolutely ideal locations in Berkshire Co. You are a 10 minute drive to Tanglewood (and away from all the traffic jams in Lenox and Lee) a walk to Stockbridge center, and Great Barrington is just down Route 7 a few miles. People who want to go to the theatre in Stockbridge or concerts at Tanglewood are nuts not to stay here. If you are not into a breakfast with 5 …

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$150

4 BR / 1 BA / Sleeps 7

19 Reviews

$150

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Gartner House, a charming home in Lenox

Lenox condo – 18.8 mi away
4 BR / 1 BA / Sleeps 7 | Quick view
Excellent19 Reviews

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Reviews

(19)

Located on a quiet side street in the charming Berkshire town of Lenox, Gartner House is a great place to call home while exploring this scenic, historical, and culturally rich area of Western Massachusetts. Walk to breakfast, lunch or dinner at one of the town's many charming restaurants, explore quirky little shops …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Suitable for children - ask

Details

Reviews

(19)

Quaint & Cozy Condo!

Left on Jan 10, 2012 for a stay in December 2011

Having stayed at Gartner House a few times, I would recommend it to anyone looking for a comfortable getaway. It is a convenient, short walk to the center of Lenox allowing easy access to all of the wonderful little shops and some great places to eat.
The condo offers all the comforts of home including full kitchen, land line phone, microwave, washer/dryer and a small side yard. Its spacious …

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$499

4 BR / 4 BA / Sleeps 12

2 Reviews

$499

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Beautiful New Construction Vacation Home

Stockbridge house – 13.0 mi away
4 BR / 4 BA / Sleeps 12 | Quick view
Excellent2 Reviews

Details

Reviews

(2)

We call this house ‘South Sedgwick’ because of its location on a piece of land formerly used by the Sedgwick family for picnicking–an ideal spot for relaxation with stunning views of Monument Mountain and Ice Glen. The house is newly constructed with ash hardwood floors, custom white pine trim and mahogany …
  • Mountain Views
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(2)

A true gem. New and beautiful with incredible space and wonderdul amenities, right in the heart of

Left on Jul 18, 2014 for a stay in July 2014

Our family of 5 rented this home over July 4th weekend and we couldn't have been more pleased. The home has just been newly renovated, is very tastefully appointed and looks and feels brand new both inside and out. It also has every amenity we could've hoped for, such as state-of-the-art kitchen appliances, wi-fi, cable TV plus Netflix, dual zone central air, a nice gas grill, multiple outdoor…

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$150

1 BR / 1 BA / Sleeps 2

1 Reviews

$150

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the yellow room at the chestnut lodge

Lee B&B – 17.1 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

first floor queensized bed, bath with shower. floors are wood ceiling has exposed beams and is furnished with oak antiques and a big wingbacked chair.built in bookshelf was from a companionway on a wooden sailing vessel owned by a sea captain that owned and ran the lodge back at the turn of the 20th century. the …
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

I have stayed here several times

Left on Jun 17, 2014 for a stay in June 2013

And I hope to stay here again in the future. I feel very comfortable here - good privacy, the house is huge, rustic charm, generally very quiet. The property is massive - and the region is one of the most beautiful in the world.

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$450

1 BR / 1 BA / Sleeps 2

1 Reviews

$450

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rustic Chestnut Lodge! vintage Berkshires home !

Lee B&B – 18.3 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

handsome and welcoming, this authentic Berkshire lodge will make you feel like you`re in an old fashioned Christmas card! fireplace blazing, wood floors post and beam, hand planed planks. in the kitchen the floor is marble slabs from the famous lee marble quarry. Daniel Chester French, the designer of the Lincoln …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Beautiful, historic, atmospheric, peaceful, getaway lodge.

Left on Jun 12, 2014 for a stay in August 2013

I had several summer months here, it never disappoints. Full of nature's bounty, hospitable host, friendly vacationers. Very close to all the best of the Berkshires, Tanglewood, dance, theater, Shakespeare, art, homes of historical writers and sculptors. Or just relaxing and reading and often game nights. Smoke free. I look forward to my return.

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$200

1 BR / 1 BA / Sleeps 2

1 Reviews

$200

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Writer's Room at Chestnut Lodge

Lee B&B – 17.0 mi away
1 BR / 1 BA / Sleeps 2 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

The Writer's Room is at the top of the stairs on the right. This handsome room is made completely of wood. Ceilings are higher and there's a sitting area in the big dormer. dormer faces east and get the morning sun! The floors are wide plank cherry milled from the property. the walls are pine. there's a double bed, a…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

vintage New England...home and hearth, the nearby arts and surrounding countryside

Left on Jun 17, 2014 for a stay in June 2013

We have taken the Writer's Room each Summer for about three years now. We find the Lodge to be authentic New England... our natural wood room to the rest of the house. It is rustic 18th century all the way.

We either make our own meals or join in with others...cooking indoors and eating at the big banquet table, or outside at the BBQ.

We love the arts...Jacob's Pillow for dance, …

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$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

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Renovated Early 1800s Greek Revival Farmhouse

Stockbridge house – 13.3 mi away
3 BR / 2 BA / Sleeps 6 | Quick view
Excellent1 Reviews

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Reviews

(1)

Welcome to our family getaway in the Berkshires which we also rent out. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to the Norman Rockwell Museum, Chesterwood House, and Botanical Gardens. The sunny 1st floor features a living room with fireplace open to…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area

Details

Reviews

(1)

Awesome home and great getaway destination!

Left on Jan 22, 2015 for a stay in October 2014

This home has everything. It also happens to be a wonderfully furnished home. The home owner left little treats for us as we arrived late the first night.

The surrounding towns had great food, fun music, good hiking, solitude and peaceful spots to stop and take in the great views!

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$500

3 BR / 3 BA / Sleeps 8

1 Reviews

$500

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Fall/ Winter- Spectacular Setting-Family- Ski Sled Hike Fish Relax

Stockbridge house – 14.2 mi away
3 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

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Reviews

(1)

A home for the family: SKIING, SNOWSHOEING, AND SLEDDING. Fall and Winter availability. Behind the house, on the property is a HUGE hill that is great for sledding. 12 mins to Butternut. 25 mins to Jiminy. Across the road is a park that is great fun to hike, snowshoe, CC ski, and explore. A 1/4 mile driveway …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for the elderly

Details

Reviews

(1)

A little piece of paradise!

Left on May 18, 2010 for a stay in July 2009

This house had it all... my wife and I loved our time there. During the day we would either sit on the deck and read or go swimming in our own private lake that was very, very clean. It was close to town for us to go shopping and there were lot's of places to take walks and things to see and do. At night we would make a fire outside in the fire pit and we would soak in the hot tub. The house was …

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$175

3 BR / 2 BA / Sleeps 7

13 Reviews

$175

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Berkshires House, 40 wooded acres, Lake Frontage

Monterey house – 11.8 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
Excellent13 Reviews

Details

Reviews

(13)

Charming house with the feeling of a cottage, set on a knoll with adjacent cathedral-like pine forest. ** Stone fireplace, woodstove, beautiful kitchen with modern appliances (gas stove, microwave, refrigerator with water/ice dispenser, dishwasher, breadmaker, crockpot, blender, etc.) ** Cathedral-ceiling living area…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(13)

Awesome Venue!

Left on Jul 17, 2012 for a stay in June 2012

The Hill Cottage is absolutely charming. It is nestled in the forest surrounded by soaring, magnificent pines on a private country road. The atmosphere is very tranquil and peaceful. The cottage is spacious, clean, and well stocked.It is very comfortable and inviting. The cottage is rustic with attractive wide pine floors and knotty pine walls, yet it has very modern amenities including a Jacuzzi…

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$250

3 BR / 3 BA / Sleeps 7

5 Reviews

$250

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Perfect Location Perfect House Perfect Vacation

West Stockbridge house – 17.3 mi away
3 BR / 3 BA / Sleeps 7 | Quick view
Excellent5 Reviews

Details

Reviews

(5)

Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private Visit our web-site at aberkshirehome The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a destination…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(5)

A memorable weekend getaway includes the most perfect house..

Left on Apr 17, 2013 for a stay in July 2012

My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly…

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$225

3 BR / 2 BA / Sleeps 7

4 Reviews

$225

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Family-friendly Cottage Near Lake, Tanglewood

Stockbridge cottage – 16.4 mi away
3 BR / 2 BA / Sleeps 7 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

Located a short walk to the town beach on the Stockbridge Bowl, and 1.5 miles from Tanglewood's Hawthorn entrance, this casual summer cottage is a great get away for the whole family. The master bedroom is equipped with a queen bed; two twins in the 2nd bedroom, and a full-size bed in the 3rd bedroom. A sofa in the …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

Hidden Gem

Left on Jul 18, 2013 for a stay in July 2013

I would like to tell you not to go here. I would like to say stay away, that way it will be availible whenever we want to go back. It is the perfect place to use as a centre to see the area, or sit and do nothing. It was my wife, kids and grand mothers. We did hike, we did spend a day on the beach right by the house, but we also felt at ease to just sit on the screened porch and play cards or …

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$375

5 BR / 4 BA / Sleeps 10

2 Reviews

$375

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Shaker Hill

Great Barrington house – 11.3 mi away
5 BR / 4 BA / Sleeps 10 | Quick view
Very Good2 Reviews

Details

Reviews

(2)

Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fields, diverse wetlands, wildlife and forest. It…
  • Mountain Views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(2)

Big house, private, but a few drawbacks

Left on Sep 11, 2014 for a stay in August 2014

This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window. The playroom is a nice touch for those with kids. There are two staircases, which is also nice.

I was under the impression that there were four full bathrooms (which I took to mean with showers). When we arrived, we…

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$200

3 BR / 2 BA / Sleeps 8

1 Reviews

$200

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Stockbridge Bowl house

Stockbridge house – 16.0 mi away
3 BR / 2 BA / Sleeps 8 | Quick view
Average1 Reviews

Details

Reviews

(1)

3-bedroom home on lake, near Tanglewood. 2 baths, den, screened porch, large yard.
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Great location, tired house

Left on Jul 30, 2014 for a stay in July 2014

Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus. With a little updating and a good cleaning,it could be fantastic.

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$600

2 BR / 2 BA / Sleeps 5

3 Reviews

$600

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July 26 to August 2 Berkshire Oak & Spruce resort

Lee condo – 13.8 mi away
2 BR / 2 BA / Sleeps 5 | Quick view
Very Good3 Reviews

Details

Reviews

(3)

Prime week 2br 2ba Berkshire Oak & Spruce resort time share. Full amenities indoor and outdoor pools. Tennis, basketball, mini golf, game room, movie theater on resort. A short drive to tangle wood, lakes etc.
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(3)

Peaceful, Quiet, and Scenic

Left on Jun 25, 2014 for a stay in June 2014

I was planning to spend the week traveling around the upper Northeast of the US (Conn, Rhode Island, New Hampsire, Vermont, Maine, and New York.) I chose this resort based on its central location and that it had two bedroom/two bath untis available.

Other than checking in late at night (quite efficient and pleasent by the way), the only other contact I had with resort staff was the minor …

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$250

5 BR / 3 BA / Sleeps 12

1 / 5

$250

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Lakefront Chalet On Pristine Lake/Nature Preserve

Granville chalet – 16.8 mi away
5 BR / 3 BA / Sleeps 12 | Quick view

Details

4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining 4 Bedrooms, 3 Baths, 3 Guest Rooms, Open Floor Plan Kitchen, Living, Dining Lakefront, 4 bedrooms, 3 baths, 3 guest rooms, open floor plan with kitchen, living and dining areas, family room, sports room, deck, two balconies and patio. The …
  • Waterfront
  • Ocean or water views
  • Outdoor Dining Area
  • Central heating
  • Deck
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

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$643

6 BR / 6 BA / Sleeps 12

1 / 25

$643

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Berkshire Estate: Exquisitely furnished 7,000sf

Great Barrington villa – 11.4 mi away
6 BR / 6 BA / Sleeps 12 | Quick view

Details

This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 7,000 sf of living space (3 floors) with plenty of places to be together or to be alone (as one so chooses). It is on 9 …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

5 BR / 3 BA / Sleeps 12

1 / 10

$300

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Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse / barn – 16.2 mi away
5 BR / 3 BA / Sleeps 12 | Quick view

Details

Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 people and is fully equipped. There's a sewing …
  • Mountain Views
  • Wireless Internet
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Suitable for children

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$350

5 BR / 3 BA / Sleeps 10

1 / 9

$350

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Berkshire Lakefront House

Great Barrington house – 10.7 mi away
5 BR / 3 BA / Sleeps 10 | Quick view

Details

Attractive year-round lakefront house in a wooded area on a pristine Round Pond in the Berkshires. Relax and enjoy the view from your deck or dock. Fish from the dock or take the boat out onto the lake. Ideal family retreat in Great Barrington and only a short drive to cultural attractions (Tanglewood, Rockwell Museum…
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$650

4 BR / 6 BA / Sleeps 12

1 / 22

$650

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Country Elegance in the Berkshires

Great Barrington house – 9.7 mi away
4 BR / 6 BA / Sleeps 12 | Quick view

Details

This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as lakes, hiking, movies, theater, shops, …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$175

2 BR / 2 BA / Sleeps 6

1 / 4

$175

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Berkshires Rental 15 minutes to Tanglewood

South Lee condo – 13.6 mi away
2 BR / 2 BA / Sleeps 6 | Quick view

Details

Two Bedroom two bathroom condo located on beautiful resort in the Berkshires. Oak and Spruce Resort located 15 minutes to Tanglewood is the summer home in the Berkshires of the Boston Symphony Orchestra. Condominium sleeps 6 with an eat in kitchen and living area. Recreational activities, ample parking located in …
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$225

1 BR / 1 BA / Sleeps 2

1 / 8

$225

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Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage – 14.1 mi away
1 BR / 1 BA / Sleeps 2 | Quick view

Details

Charming, One Bedroom Cottage, former sculpting studio on the Santarella Estate in Tyringham, MA. Known as the "Silo Studio", there is a bedroom with queen bed upstairs, sitting room, wet bar with Micro/Fridge and bath downstairs. Fall asleep to sounds of babbling brook and views to pond and forest from large screened…
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Balcony or terrace
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$400

4 BR / 2 BA / Sleeps 10

1 / 18

$400

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LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

Lenox house – 16.6 mi away
4 BR / 2 BA / Sleeps 10 | Quick view

Details

220+ Acres W\ Tennis Cts, Indoor / Outdoor Pool, Canoe, Fishing Boat, Hot Tub. New first time rental of 4 BR, 2BA, Cape Cod style, sleeps 10-12. New fully equipped kitchen w/ center island, indoor and outdoor barbecues, wine cooler, 2 fireplaces, large deck with 8 person hot tub and super seating for beautiful sunsets…
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$250

5 BR / 3 BA / Sleeps 12

1 / 21

$250

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Beautiful Berkshire post and beam house

Monterey house – 12.4 mi away
5 BR / 3 BA / Sleeps 12 | Quick view

Details

This is a beautiful Berkshire, post and beam private house nestled in the woods just off the Appalachian trail. Set on one of the Berkshires most coveted roads close to fresh water swimming in Lake Garfield, boating, fishing, classical outdoor concerts at Tanglewood & Skiing are all close by. The Space The large …
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$129

1 BR / 2 BA / Sleeps 4

1 / 12

$129

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Berkshires Resort Apartment

South Lee condo – 13.6 mi away
1 BR / 2 BA / Sleeps 4 | Quick view

Details

RIght off the Mass Pike Exit 2, Berkshire family vacation condo with full kitchen and all amenities.Take in Boston Symphony at Tanglewood and dance at Jacob's Pillow, theatre at Shakespeare & Company, Yoga at Kripalu, a spa day at Canyon Ranch, the Norman Rockwell Museum, Hancock Shaker Village, Edith Wharton's The …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$122

2 BR / 2 BA / Sleeps 4

1 / 6

$122

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Berkshires on the Pond

Becket house – 18.4 mi away
2 BR / 2 BA / Sleeps 4 | Quick view

Details

Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water view. Bedroom sleeps …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for the elderly - ask

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$500

3 BR / 2 BA / Sleeps 6

1 / 11

$500

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Vacation Home on 10 Acres with Pool and Spa

Stockbridge house – 14.5 mi away
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Vacation home centrally located in the Berkshires, 1 mile from Norman Rockwell and 3 miles from Tanglewood, on a quiet country road. Spacious grounds with large 2-level deck overlooking gardens and woods, private in-ground pool with pool house and deck, hot tub. House includes 3 bedrooms, 2 newly renovated baths, …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

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$179

0 BR / 2 BA / Sleeps 7

1 / 11

$179

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Fabulous Post & Beam Berkshire Rental

Monterey house – 8.3 mi away
0 BR / 2 BA / Sleeps 7 | Quick view

Details

You'll love our hand-hewn post & beam beauty on 13 acres in the Berkshire Mountains of Western Mass located near the Monterey/Great Barrington line, close to everything. Great for summer and winter ski season. Rich in both outdoor and cultural attractions, shopping and antiquing. Located adjacent to legendary …
    • Pet friendly - ask
    • Smoking allowed - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $175

    1 BR / 1 BA / Sleeps 2

    1 / 2

    $175

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    chestnut lodge Queens Room

    Lee B&B – 17.0 mi away
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    Sunny, light , bright and wide! the queens room is one of the biggest rooms and has private ensuite bathroom with tub/shower. 2 big closets, large writing desk, comfy conversation area, 2 dressers full sized bed. a section of the room has original ceilings so persons taller than 6'2" would be happier in the writer'…
    • Pet friendly - ask
    • Suitable for the elderly - ask

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    $575

    3 BR / 3 BA / Sleeps 5

    1 / 5

    $575

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    Artist designed luxury in Stockbridge

    Stockbridge house – 16.1 mi away
    3 BR / 3 BA / Sleeps 5 | Quick view

    Details

    Private setting on over three acres, this artist designed and newly renovated home has cathedral ceilings in all rooms. It features a luxurious and spacious master bedroom suite with jacuzzi tub & outdoor shower Skylights are everywhere and designed to let in the light and mountain views from every room. Relax in …
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly
    • Wheelchair accessible

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    $130

    1 BR / 1 BA / Sleeps 4

    1 / 16

    $130

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    Cultural Playground 1 bed, walk to Red Lion Inn.

    Stockbridge condo – 13.4 mi away
    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    One bedroom air conditioned apartment with private entrance in 18th century house in Historic District of Stockbridge. Wonderful views of the river, 18th green of Stockbridge Golf Club and the Berkshire Hills. 5 minutes walk to the famous Red Lion Inn/town center. Self contained and private. You have private bedroom …
    • Waterfront
    • Wireless Internet
    • Outdoor Dining Area
    • A/C or climate control
    • Central heating
    • Pet friendly - ask
    • Suitable for children
    • Suitable for the elderly - ask
    • Wheelchair accessible - ask

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    $250

    3 BR / 2 BA / Sleeps 8

    1 / 19

    $250

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    Maya's Garden House

    Great Barrington house – 7.3 mi away
    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Surrounded by one of the most beautiful gardens in the Berkshires, Maya's Garden House is an outstanding example of an 18th century barn converted into a modern, comfortable, semi-secluded home. Located less than a mile from Great Barrington, it is close to everything the Berkshires are famous for; Tanglewood, Jacob's…
    • Mountain Views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Outdoor Dining Area
    • Pet friendly
    • Smoking allowed - ask
    • Suitable for children
    • Suitable for the elderly

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    $750

    5 BR / 5 BA / Sleeps 12

    1 / 7

    $750

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    Deluxe New Home, 2 Master Suites, Tanglewood Area

    Lee house – 16.6 mi away
    5 BR / 5 BA / Sleeps 12 | Quick view

    Details

    --Brand new 3400 sq ft Lee home in a private lake community, Berkshires --Situated on 4 wooded acres on a quiet country road --Pristine home features two master bedroom suites plus 3 additional bedrooms, 5 bathrooms --Spacious living room with vaulted ceiling & skylights --Fully equipped kitchen, --New 25' Dining …
    • Suitable for children
    • Suitable for the elderly

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    $500

    4 BR / 3 BA / Sleeps 8

    1 / 15

    $500

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    Charming and Spacious Colonial Farmhouse on 4 Acre Estate

    Tyringham villa – 14.1 mi away
    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Located on the Santarella Estate, an historic site located in the the Massachussetts' Berkshires. The colonial home is the former residence of sculptor Sir Henry Hudson Kitson. The estate includes the landmark, iconic storybook style 'Gingerbread House,' designed by Kitson to look like an English Country Cottage, the …
    • Mountain Views
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Washing Machine
    • Suitable for children
    • Suitable for the elderly
    • Wheelchair accessible - ask

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    $250

    1 BR / 1 BA / Sleeps 4

    1 / 8

    $250

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    Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

    Tyringham house – 14.1 mi away
    1 BR / 1 BA / Sleeps 4 | Quick view

    Details

    Santarella Estate and Gardens in Tyringham, MA is a magical destination in the heart of one of the Berkshires' most beautiful valleys, located 3 miles from Interstate 90 and 15 minutes from most of the principal attractions (Tanglewood, Jacob's Pillow, Norman Rockwell museum, etc.) Pictures are worth a thousand words…
    • Pet friendly - ask
    • Suitable for children - ask
    • Suitable for the elderly - ask
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