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Charming Berkshires lakefront house, great views - Berkshires vacation rentals
1 / 19

$200

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Charming Berkshires lakefront house, great views

Cheshire house
2 BR / 1 BA / Sleeps 5 | Quick view

Details

Comfortable house situated on the shore of Hoosac Lake with beautiful, long views stretching across the large lake. It's fully furnished, with cable TV, stereo, and high-speed Internet. There's a big kitchen, with a central island for dining. The expansive living/dining room and attached study, with distinctive wood …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly - ask

$189

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Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock condo
2 BR / 2 BA / Sleeps 6 | Quick view
Very Good1 Reviews

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Reviews

(1)

A fully furnished and nicely appointed 2br/2ba suite. There's a full kitchen, living room with sofa sleeper, king bed in master bedroom, 2nd bedroom has either a king bed or two queen size beds(varies), washer/dryer, private balcony with mountain or valley views. Everything you need on your vacation. Free parking and…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Beautiful area in the fall

Left on Oct 25, 2014 for a stay in October 2014

Lovely place with pool, spa, gym, and movie theater. Units are a bit noisy between floors but otherwise nice and quiet. We had the unfortunate experience of having three small children above us. They enjoyed running and moving furniture. Oh well. Still had a nice stay despite that and a couple of days of rain.

$150

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Stone School Cottage

Lanesboro cottage
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent12 Reviews

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Reviews

(12)

If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a vacation getaway. It is perfect for romantic weekends or family adventures. We are …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Suitable for children

Details

Reviews

(12)

Great location, with wonderful scenic spots very close by

Left on Oct 17, 2011 for a stay in October 2011

The best thing about this place was the location. We came here to see the foliage, and we didn't have to go anywhere else driving around looking for it. This is right on the road to Mt Greylock which has so many hiking trails and scenic overlooks.

The Old Stone School cottage is a quaint setup, and the classroom doubles as a bedroom. This is not much of a bedroom, but just a big room with 2 …

Berkshire Lakefront House - Berkshires vacation rentals
1 / 9

$350

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Berkshire Lakefront House

Great Barrington house
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

$100

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Yankee Suites Extended Stays

Pittsfield condo
1 BR / 1 BA / Sleeps 5 | Quick view
Excellent1 Reviews

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Reviews

(1)

A Fully-Furnished Extended Stay property in the Berkshires. Located across the street from the Colonial Theatre and within minutes of most Berkshire County attractions. Each spacious, efficiency (condo-style) single bedroom apartment includes living room, kitchen with full size appliances, bathroom, and deck. Enjoy …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Excellent Rooms Plus Exceptional Service

Left on Jul 03, 2013 for a stay in January 2013

WOW, this place was very nice! What you get is a place with a five minute walk from downtown, well kept buidlings and grounds, excellent floor plans, new furniture, modern kitchen, large closets, a lot of storage space, outside deck, deckbawasher and dryer in the basement, latest technology i.e. cable TV, internet, maid service twice a week.

Plus a friendly staff on-site seven days a week …

$250

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Berkshires Spacious Comfortable Charming Farmhouse

Lee condo
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.

1 / 8

$130

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house
3 BR / 2 BA / Sleeps 7 | Quick view

Details

Located on 19 acres of forest and a creek, mixing modern and traditional with a charming two story wall of windows overlooking a back deck. This comfortable furnished home has two bedrooms with an additional open loft area for a third bedroom, two baths, all hardwood floors, and contains a large kitchen with all new …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
1 / 8

$432

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Hawk Mountain Lodge at Zoar Outdoor

Charlemont house
5 BR / 3 BA / Sleeps 14 | Quick view

Details

Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski Resort, our …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Central heating
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible
1 / 16

$350

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Berkshire Waterfront Home

Becket house
3 BR / 2 BA / Sleeps 5 | Quick view

Details

Lovey 3 Bedroom house on 200 acres in the Beautiful Berkshires. Drive in, close the gate and enjoy the privacy, sunny lawn leading to a small private lake for swimming, canoeing, fishing. Fully furnished and stocked with everything you need for a stay with family or friends. New bathrooms and kitchen, Pine Cone …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
1 / 6

$122

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Berkshires on the Pond

Becket house
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

$225

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2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house
4 BR / 2 BA / Sleeps 10 | Quick view
Excellent3 Reviews

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Reviews

(3)

Come and enjoy our beautiful mountain retreat - A home for every season. This charming home away from home is a wonderful place for family, friends and romance. Only 3 minutes from Jiminy Peak! With over 2200 square feet, this new country home has plenty of space for everyone yet a very cozy feel. Each one of the 3…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(3)

Had a great time!

Left on Oct 07, 2010 for a stay in August 2010

The house was very clean and well supplied. The location is very convenient to fun family activities.

$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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Reviews

(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

Details

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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$250

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Maya's Garden House

Great Barrington house
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
1 / 10

$250

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Josiah Loomis Homestead

Richmond house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

In 1832, Josiah Loomis bought a parcel of land "and the structures thereon", along what was then known as "Massachusetts Turnpike No. 10," the toll road between Albany, NY and Hartford, CT. Josiah Loomis, when he owned this property, could never have imagined what it would look like 180 years later. His 3 room …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask
1 / 16

$300

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Charming Home Nestled in the Berkshires

Becket house
3 BR / 4 BA / Sleeps 6 | Quick view

Details

Charming 3 bedroom home nestled on 5 acres of secluded woods in the beautiful Berkshire Mountains. Located in the lovely town of Becket on a private road. Completely updated home with a large, open floor plan. Master bedroom with attached private full bathroom on first floor, two additional bedrooms on second …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly

$140

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Lakeside 2Bedroom Home in the Beautiful Berkshires

Richmond house
3 BR / 1 BA / Sleeps 7 | Quick view
Poor1 Reviews

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Reviews

(1)

The Berkshires, in Western Massachusetts, are known as center of cultural activities, including but not limited to Tanglewood (the summer home of the Boston Symphony Orchestra), Shakespeare Theatre Festival, Jacobs Pillow, Williamstown Theatre Festival, plus numerous recreational opportunities for hiking, swimming, …
  • Ocean or water views
  • Internet Access
  • Housekeeping Optional
  • Balcony or terrace
  • Parking
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Major Let Down

Left on Sep 10, 2014 for a stay in August 2014

I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The owners require that you pay a $75 cleaning fee, but the house was clearly not cleaned before we arrived. The owners also mailed the wrong keys, so we were locked out of the house after Tanglewood until about midnight when …

1 / 12

$250

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Charming, secluded 1860's farmhouse

Lenox house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Charming, spacious and comfortable 1860's farmhouse adjacent to wildlife sanctuary. Cozy country decor with original wide plank floors, lovely views and outdoor dining or lounging on porch or deck. Walking distance to hiking trails in Pleasant Valley Wildlife Preserve or Kennedy Park. Quiet and private, yet …
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly - ask

$100

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Race Mountain House

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

Details

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 …

1 / 4

$175

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Berkshires Rental 15 minutes to Tanglewood

South Lee condo
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
1 / 8

$250

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Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

Tyringham house
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

$450

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rustic Chestnut Lodge! vintage Berkshires home !

Lee B&B
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.

1 / 2

$175

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chestnut lodge Queens Room

Lee B&B
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
1 / 7

$200

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the BIG room at chestnut lodge

Lee B&B
1 BR / 1 BA / Sleeps 6 | Quick view

Details

sleeps 4 can combine with writer's room for large suite, private entrance. fireplace or windowed woodstove, ceiling fans cathedral ceiling, terrace with seating, pasture and forest views. windows line both sides of room and feels like a treehouse. beautiful wood floors and soft carpets make you feel right at home, …
  • Pet friendly
  • Suitable for children - ask
1 / 10

$125

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ground floor garden room

Lee B&B
1 BR / 1 BA / Sleeps 2 | Quick view

Details

the garden room is a small room with a full sized bed. everything is floral, even the closet walls. it 's a sweet room with even a wood stove. it has an entrance to the courtyard just outside in the hall, the bath may be shared depending on the situation. bath has shower and lovely old sink. bath is ceramic tiled. …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • Balcony or terrace
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
1 / 11

$200

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little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

Lee cottage
1 BR / 1 BA / Sleeps 4 | Quick view

Details

cute cozy cottage, screened porch with views, close to everything, sleeps 4 . nice yard with big old trees and soft grass. gas bbq, just one mile to stockbridge center , Berkshire theatre festival. 5 miles to tanglewood, lenox , kripalu. 10 minutes to great barrington. bath has shower. full kitchen with peninsula…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

$250

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

Great Barrington house
2 BR / 1 BA / Sleeps 5 | Quick view
Excellent2 Reviews

Details

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

Details

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 …

$243

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

Great Barrington house
2 BR / 2 BA / Sleeps 4 | Quick view
Very Good1 Reviews

Details

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

Details

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 …

$143

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Lake community - Berkshires

Sandisfield house
3 BR / 3 BA / Sleeps 6 | Quick view
Excellent1 Reviews

Details

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 …

$465

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Gem of the Berkshires, walk to downtown & lake.

Great Barrington condo
4 BR / 4 BA / Sleeps 12 | Quick view
Excellent3 Reviews

Details

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…

$100

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The House in Pumpkin Hollow B&B

Conway house
2 BR / 1 BA / Sleeps 4 | Quick view
Excellent4 Reviews

Details

Reviews

(4)

The House in Pumpkin Hollow Bed and Breakfast is nestled in the foothills of the Berkshires in Conway, Masschusetts. It is surrounded by woods. fields, and other historic homes. Ideally situated 6 miles off Route 9, it is close to Northampton, Deerfield, Brattleboro, Amherst and Shelburne Falls. This spacious, 1860 …
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Lovely Stay

Left on Apr 03, 2014 for a stay in October 2013

We so enjoyed our stay at The House in Pumpkin Hollow in the sweet town of Conway. We needed a getaway and it was perfect. Diane and her darling dogs greeted us, and she was available for any questions we had. She's a warm and engaging host. The house is stunning with beautiful decor, antiques, large windows and a curving staircase up to our rooms. It was quiet and very private. Nice restaurants …

$275

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Escape to the Berkshires!

Becket house
4 BR / 3 BA / Sleeps 8 | Quick view
Excellent1 Reviews

Details

Reviews

(1)

Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our local lake is a …
    • Pet friendly
    • Suitable for children
    • Suitable for the elderly

    Details

    Reviews

    (1)

    Fabulous Getaway!

    Left on Aug 29, 2014 for a stay in August 2014

    This was our first trip to the Berkshires and we feel fortunate to have found this fabulous home. It suited our needs perfectly as we were traveling with kids and grandparents. The house is set up ideally for this arrangement since there are bedrooms on either side of the house with living room, kitchen, and dining area in the middle. This gives everyone plenty of privacy. We also really …

    $500

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

    Stockbridge house
    3 BR / 3 BA / Sleeps 8 | Quick view
    Excellent1 Reviews

    Details

    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 …

    $600

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    July 26 to August 2 Berkshire Oak & Spruce resort

    Lee condo
    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 …

    1 / 10

    $300

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    Comfortable Farmhouse in the Berkshires

    West Stockbridge farmhouse barn
    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
    1 / 19

    $350

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    LAKEFRONT HOME IN BERKSHIRES

    Berkshire house
    3 BR / 1 BA / Sleeps 8 | Quick view

    Details

    Berkshire Home on Goose Pond, the cleanest lake in Massachusetts. The entire house, including a fully equipped kitchen, was remodeled and professionally designed two years ago. The glass front of the house provides floor to ceiling, unobstructed, lake views. We are situated near the end of a private, quiet, …
    • Waterfront
    • Ocean or water views
    • Mountain Views
    • Fireplace
    • Washing Machine
    • Suitable for children
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    $230

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    Cill Aodain Cabin

    Great Barrington cottage
    1 BR / 1 BA / Sleeps 2 | Quick view

    Details

    One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood burning stove. Ideal base for enjoying the best of the …
    • Mountain Views
    • Internet Access
    • Fireplace
    • Deck
    • Parking
    • Pet friendly
    • Suitable for children - ask
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    $200

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    Berkshires- 2015 Summer Rental July And August

    Hancock condo
    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Luxury condo in hancock, ma ....Three bedrooms, loft, 2 baths, living room, kitchen with dining area, a/c, deck w/grill et al, heated pool, tennis court, mountain view. Near williamstown theater, clark art museum, tanglewood and three local golf courses.
    • Mountain Views
    • Sauna
    • Internet Access
    • Fireplace
    • Housekeeping Optional
    • Suitable for children
    • Suitable for the elderly
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    $179

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    Fabulous Post & Beam Berkshire Rental

    Monterey house
    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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      $575

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      Artist designed luxury in Stockbridge

      Stockbridge house
      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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      $250

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      Jiminy Peak Ski Resort-Country Village's Best Unit

      Hancock condo
      2 BR / 2 BA / Sleeps 6 | Quick view

      Details

      Two Bedroom Ski Condo at base of Jiminy Peak. Renovated kitchen, fireplace, deck and a large livingroom with vaulted ceilings. Rent from the owner and save.
      • Fireplace
      • Housekeeping Optional
      • Central heating
      • Linens Provided
      • Towels Provided
      • Suitable for children
      • Suitable for the elderly - ask
      • Wheelchair accessible - ask
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      $500

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      Vacation Home on 10 Acres with Pool and Spa

      Stockbridge house
      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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      $175

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      Berkshire Cottage

      Windsor cottage
      2 BR / 1 BA / Sleeps 6 | Quick view

      Details

      Peaceful, mountain hideaway. Rural, yet easily accessible to all major Berkshire County and Pioneer Valley attractions. Recently renovated, this charming 2-bedroom cottage can comfortably accommodate 4-6 people or could be a romantic retreat for two. Full kitchen with all appliances gives you the option of cooking …
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
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      $195

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      Spacious wooded home

      Becket house
      4 BR / 6 BA / Sleeps 12 | Quick view

      Details

      Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating activities and a beach …
      • Central heating
      • Balcony or terrace
      • Parking
      • Grill
      • Linens Provided
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      $130

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      Solid Rock Farm

      Stockbridge farmhouse barn
      3 BR / 3 BA / Sleeps 8 | Quick view

      Details

      Our 1762 Farmhouse is lovingly being restored with gardens in the Berkshires. Mission statement: Educating members in life, farming, and creative art skills acknowledging God as our provider. One mile from the Norman Rockwell Museum and 5 miles from Tanglewood. Come join the farm "Agritourism" experience!
      • Internet Access
      • Washing Machine
      • Clothes Dryer
      • Central heating
      • Parking
      • Pet friendly - ask
      • Suitable for children
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      $150

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      Hillside Hideaway with Trout Stream

      Becket house
      3 BR / 1 BA / Sleeps 5 | Quick view

      Details

      You can 'have it all' in the Berkshires! Our cozy contemporary home is less than 30 minutes from all Berkshire cultural and historical attractions, but tucked away in woodsy peace and privacy. Our four acres look out over a large lawn, lovely flower and herb garden, old apple orchard, and trout stream to a facing …
      • Suitable for children
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      $445

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      House On Main Street

      Williamstown house
      5 BR / 5 BA / Sleeps 16 | Quick view

      Details

      Lots of space, great yard, plus you can walk to everything: restaurants, museums, Williams College, theater, night life, etc. This beautifully maintained historic House On Main Street was known as the Victorian Tourist & Antique House in a by-gone era. It was originally constructed in the mid 1700's and was …
      • Wireless Internet
      • Fireplace
      • Washing Machine
      • Clothes Dryer
      • Outdoor Dining Area
      • Pet friendly - ask
      • Suitable for children
      • Wheelchair accessible - ask
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      $141

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      OWL'S NEST LODGING

      Conway condo
      1 BR / 1 BA / Sleeps 3 | Quick view

      Details

      Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study "nook", private bath with laundry facilities and a separate entrance. Guests are greeted every morning by two friendly alpacas, …
      • Mountain Views
      • Wireless Internet
      • Parking
      • Linens Provided
      • Towels Provided
      • Suitable for children - over five
      1 / 6

      $50

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      SKI HOUSE IN MONTEREY MASSACHUSETTS

      Monterey condo
      1 BR / 1 BA / Sleeps 1 | Quick view

      Details

      We rent our house for a full winter season from November through March. You can enjoy all holidays, school breaks, weekends during the winter in your own winter wonderland. Contact us for all details. Walk to charming 200 year old Monterey with library, playground, playing fields, ice skating rink.15 minutes to Great …
      • Pet friendly
      • Suitable for children
      • Suitable for the elderly
      • Wheelchair accessible - ask
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      $242

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      Spacious comfortable mid-century modern near town

      Lenox house
      3 BR / 2 BA / Sleeps 6 | Quick view

      Details

      In the heart of Lenox, this 2 BR plus study (can be used as a 3BR) house offers the best of both worlds. On nearly 2 park-like acres, the house is a peaceful place for rest and relaxation. But there's much to do nearby. The town center of Lenox is within easy walking distance so you'll be close to restaurants, shops…
      • Internet Access
      • Fireplace
      • Housekeeping Optional
      • Washing Machine
      • Clothes Dryer
      • Pet friendly - ask
      • Suitable for children
      • Suitable for the elderly
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      $270

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      Wyndham Bentley Brook (Jiminy Peak mountain)

      Hancock resort
      2 BR / 2 BA / Sleeps 8 | Quick view

      Details

      Exclusive Deal for Christmas week, the most wanted week of the year! Ski-In/Ski-Out Plus Year-Round Mountainside Fun! Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. During the winter, ski out your door and onto the lifts…
      • Mountain Views
      • Hot Tub/Jacuzzi
      • Sauna
      • Wireless Internet
      • Washing Machine
      • Suitable for children
      • Suitable for the elderly - elevator access
      • Wheelchair accessible - ask
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