Showing

PreviousNext property

$135

3 BR / 1 BA / Sleeps 6

4 Reviews

$135

Book

Lakeview home with swingset & firepit!

3 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Fantastic spot for families and for those looking for a quiet getaway. Come have some summer fun, enjoy the autumn colors or play in the snow. This year round cottage is the perfect spot for those who enjoy outdoor activities. The house is on a private dead end road, has a wonderful lake view and very private …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(4)

Best little hidden treasure

Left on Jul 07, 2010 for a stay in June 2010

We contacted the owners on a referal from a friend and had all our questions answered and more in regards to the propery and its amenities . Upon our arrival we got out of the car and was immediately greeted with a spectacular view of the lake. The house , was immaculate , clean , organized and big enough for me and my family to feel at home. We had a fantastic vacation and I would highly …

PreviousNext property

$499

4 BR / 4 BA / Sleeps 12

2 Reviews

$499

Book

Beautiful New Construction Vacation Home

4 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 2 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…

PreviousNext property

$175

2 BR / 1 BA / Sleeps 4

12 Reviews

$175

Book

Stone School Cottage

2 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 12 Reviews

Details

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 …

PreviousNext property

$200

2 BR / 1 BA / Sleeps 4

Retreat in the Woods - Berkshires vacation rentals
1 / 6

$200

Book

Retreat in the Woods

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and other hiking trails …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Porch
  • Parking
  • Suitable for children - over five
  • Suitable for the elderly - ask

PreviousNext property

$250

3 BR / 2 BA / Sleeps 8

Maya's Garden House - Berkshires vacation rentals
1 / 19

$250

Inquire

Maya's Garden 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
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$360

5 BR / 3 BA / Sleeps 11

8 Reviews

$360

Book

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

5 BR / 3 BA / Sleeps 11 | Quick view
“ Very Good ” 8 Reviews

Details

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 …

PreviousNext property

$250

3 BR / 2 BA / Sleeps 6

1 Reviews

$250

Inquire

Renovated Early 1800s Greek Revival Farmhouse

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

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!

PreviousNext property

$130

3 BR / 2 BA / Sleeps 7

1 / 8

$130

Book

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

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

PreviousNext property

$250

5 BR / 2 BA / Sleeps 12

12 Reviews

$250

Book

Berkshire Farmhouse Vacation

5 BR / 2 BA / Sleeps 12 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

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

Details

Reviews

(12)

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. …

PreviousNext property

$250

3 BR / 3 BA / Sleeps 7

5 Reviews

$250

Book

MARCH MADNESS Weekend Special Rate Spring Skiing

3 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 5 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…

PreviousNext property

$185

1 BR / 1 BA / Sleeps 2

3 Reviews

$185

Book

The Smith Farm Homestead

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 3 Reviews

Details

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

Details

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.

PreviousNext property

$650

4 BR / 6 BA / Sleeps 12

1 / 22

$650

Book

Country Elegance in the Berkshires

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

PreviousNext property

$400

4 BR / 2 BA / Sleeps 10

1 / 18

$400

Book

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

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

PreviousNext property

$500

4 BR / 3 BA / Sleeps 8

1 / 18

$500

Book

BEAUTIFUL LINDAL CEDAR HOME WITH GREAT LAKE VIEW

4 BR / 3 BA / Sleeps 8 | Quick view

Details

The best place in the world to watch the sunset! Set up high on a hill and nestled amidst the pine trees, this four year old, private and spacious contemporary home overlooks Lake Ashmere (across the road) in Hindsdale. The great room with cathedral ceilings and a wall of windows overlooking the lake, is open to the …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$357

5 BR / 5 BA / Sleeps 12

1 / 23

$357

Inquire

Elegant 6000+Sf Luxury Estate on 13+ Park

5 BR / 5 BA / Sleeps 12 | Quick view

Details

This Elegant Luxury Estate offers 6000+ SF of Living Space on 13+ park-like, sunny acres located within only minutes from the downtown Great Barrington. This fantastic home offers 5 Bedrooms, 4.5 bathrooms, sweeping dual staircase ending with the magnificent open gallery, the kitchen offers the magnificent, high end …
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$275

4 BR / 3 BA / Sleeps 8

1 Reviews

$275

Book

Escape to the Berkshires!

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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 …

PreviousNext property

$300

6 BR / 3 BA / Sleeps 11

1 / 9

$300

Inquire

Beautiful Colonial in Secluded Berkshires

6 BR / 3 BA / Sleeps 11 | Quick view

Details

Enjoy the Fall in our New England farmhouse! Cross country ski at Canterbury Farms, only 5 minutes away! Beautifully restored Colonial historical farmhouse (1790) with almost 2 acres of lawn for playing croquet and hanging out in the sun. There is a small pond (unfenced) for frogs and birds. Large screened in …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Central heating
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$350

5 BR / 4 BA / Sleeps 10

2 Reviews

$350

Book

Shaker Hill

5 BR / 4 BA / Sleeps 10 | Quick view
“ Very Good ” 2 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…

PreviousNext property

$189

2 BR / 2 BA / Sleeps 6

1 Reviews

$189

Book

Berkshires Vacation Rental - Bentley Brook Resort Suite

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

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.

PreviousNext property

$70

1 BR / 1 BA / Sleeps 2

1 / 6

$70

Book

ROOM walking distance to Mass MoCa

1 BR / 1 BA / Sleeps 2 | Quick view

Details

I have a two bedroom apartment and I am renting out the spare bedroom. It is at the end of a dead end street with a huge wooded backyard that includes a grill, picnic table and two fire pits. It is walking distance to Mass MoCA and minutes from downtown Williamstown and/or downtown North Adams. The spare bedroom …
  • Mountain Views
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children

PreviousNext property

$350

4 BR / 2 BA / Sleeps 9

1 Reviews

$350

Book

Field View Cottage , Convenient to All Berkshire

4 BR / 2 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

Details

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!

PreviousNext property

$157

2 BR / 2 BA / Sleeps 1

1 / 9

$157

Book

Rent Hancock Ma.2 Bedroom Vac Village Ski Condo

2 BR / 2 BA / Sleeps 1 | Quick view

Details

This is an amazing 2 Bedroom Condo located in the heart of Berkshires.. On site amenities include, Pool and Game Room. Full Kitchen, 2 Baths and a large Living Room. Western Mass known for its rich culture, which will allow to enjoy close by Jaunts like, Norman Rockwell Museum, Tanglewood etc.. Just one half mile …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$350

5 BR / 3 BA / Sleeps 10

1 / 9

$350

Book

Berkshire Lakefront 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

PreviousNext property

$150

4 BR / 1 BA / Sleeps 7

19 Reviews

$150

Book

Gartner House, a charming home in Lenox

4 BR / 1 BA / Sleeps 7 | Quick view
“ Excellent ” 19 Reviews

Details

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 …

PreviousNext property

$325

4 BR / 3 BA / Sleeps 8

1 / 21

$325

Book

Historic South Lee Schoolhouse near Stockbridge

4 BR / 3 BA / Sleeps 8 | Quick view

Details

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

PreviousNext property

$250

5 BR / 3 BA / Sleeps 12

1 / 5

$250

Book

Lakefront Chalet Located On Pristine Lake In Nature Preserve - Berkshire, Ma

5 BR / 3 BA / Sleeps 12 | Quick view

Details

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 house has a unique setting in the heart of a nature preserve and is facing an …
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$195

4 BR / 3 BA / Sleeps 7

15 Reviews

$195

Inquire

Berkshire Gorge House

4 BR / 3 BA / Sleeps 7 | Quick view
“ Excellent ” 15 Reviews

Details

Reviews

(15)

The Berkshire Gorge House sits beside the Green River above a turbulent set of cascades, on the western slopes of Mt. Greylock. This 5-bedroom house was built in 1910 by New England’s finest craftsmen. It has been recently remodeled and is offered for rent. The house offers a new kitchen with gas range, new washer/…
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(15)

A peaceful setting minutes away from action and activities

Left on Apr 16, 2012 for a stay in March 2012

A fantastic, rustic house on a wonderful piece of property with easy access to skiing and other activities at Jiminy Peak, historic Williamstown, and the rest of the Berkshires. The house has a ton of character - we especially appreciated its an abundance of rooms and space for us to host friends and family for overnight visits; the new kitchen (including new appliances) was perfect for a ski …

PreviousNext property

$450

3 BR / 3 BA / Sleeps 6

1 / 20

$450

Book

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

3 BR / 3 BA / Sleeps 6 | Quick view

Details

Newly furnished 3 bedroom (with AC) & 2 1/2 bath single family home with stunning deck and in ground pool nestled in the quiet countryside opposite a horse farm. Situated minutes from West Stockbridge convenience stores and restaurants. Property is on 2 quiet tree lined acres with an enclosed idyllic swimming pool …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$500

4 BR / 3 BA / Sleeps 8

1 / 15

$500

Book

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

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

PreviousNext property

$500

3 BR / 2 BA / Sleeps 6

1 / 11

$500

Book

Vacation Home on 10 Acres with Pool and Spa

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

PreviousNext property

$250

3 BR / 2 BA / Sleeps 8

2 Reviews

$250

Inquire

Berkshires Spacious Comfortable Charming Farmhouse

3 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 2 Reviews

Details

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.

PreviousNext property

$265

3 BR / 2 BA / Sleeps 8

3 Reviews

$265

Inquire

Rose & Goat Retreat- Mountain Top Lodge

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Spectacular views are yours from this 2000 square foot Chalet Lodge located on the 50 acre Rose and Goat Retreat on the top of beautiful Florida Mountain in the Berkshires in Western Massachusetts. Enjoy cozy evenings in front of the massive stone fireplace after a day of enjoying all that the the Berkshires has to …
  • Mountain Views
  • Fireplace
  • Outdoor Dining Area
  • Central heating
  • Deck
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - adapted

Details

Reviews

(3)

"Can we stay here for every vacation!"

Left on Feb 01, 2014 for a stay in January 2014

Those are the words of my 15 year old son, who loved every minute at the Rose and Goat Retreat Chalet Lodge!! My husband and I returned to the Rose and Goat after a lovely weekend in October at the Romantic Rose and Goat Retreat, but in the cozy apartment below the Chalet Lodge. This time we were accompanied by 5 teenagers, boys and girls, and they wanted to move right in! We had a beautiful …

PreviousNext property

$432

5 BR / 3 BA / Sleeps 14

1 / 8

$432

Book

Hawk Mountain Lodge at Zoar Outdoor

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

PreviousNext property

$445

5 BR / 5 BA / Sleeps 16

1 / 17

$445

Book

House On Main Street

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

PreviousNext property

$250

2 BR / 1 BA / Sleeps 5

2 Reviews

$250

Book

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

2 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 2 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 …

PreviousNext property

$170

1 BR / 1 BA / Sleeps 2

5 Reviews

$170

Book

RiverSong Suite In The Berkshires

1 BR / 1 BA / Sleeps 2 | Quick view
“ Excellent ” 5 Reviews

Details

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

Details

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 …

PreviousNext property

$115

1 BR / 1 BA / Sleeps 4

106 Reviews

$115

Book

Unique People & Pet-Welcoming Country Haven

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 106 Reviews

Details

Reviews

(106)

Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening the cottage in…
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

Details

Reviews

(106)

A wonderful place to stay with or without pets.

Left on Mar 15, 2012 for a stay in February 2012

The cottage is clean, full of light and simply decorated. I have stayed in frilly, cutesy, flowery places that felt downright claustrophobic. The full-size kitchen has new appliances and is stocked with everything one could want, from coffee and teas to hot cereal and a variety of fresh fruit. Pat, the proprietor, spoiled me with fresh baked English scones each morning of my stay.
It is …

PreviousNext property

$150

1 BR / 1 BA / Sleeps 5

2 Reviews

$150

Inquire

Rose and Goat Retreat - Mountain View Apartment

1 BR / 1 BA / Sleeps 5 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

50 acre mountain top property in the Berkshires located between North Adams and Charlemont, Massachusetts with mountain views and within close proximity to all kinds of outdoor recreational opportunities including beaches, swimming, whitewater rafting and kayaking, hunting and fishing, hiking and biking, skiing (…
  • Mountain Views
  • Internet Access
  • Housekeeping Optional
  • Outdoor Dining Area
  • Central heating
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Should have stayed here for my honeymoon!

Left on Nov 01, 2013 for a stay in October 2013

What could be better than a private apartment on top of a mountain in the fall in western Massachusetts with french doors open to the sunrise? Margot is a most gracious and attentive owner. Very engaging and thinking of every last detail. From the breakfast basket, bottle of wine chosen for me and sparkling water for my husband, to the full-size selection of bath products, lovely white fluffy …

PreviousNext property

$130

1 BR / 1 BA / Sleeps 4

1 / 16

$130

Book

Cultural Playground 1 bed, walk to Red Lion Inn.

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
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Central heating
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$200

2 BR / 2 BA / Sleeps 8

1 / 16

$200

Book

Wyndham Bentley Brook Jiminy Peak ski in/out

2 BR / 2 BA / Sleeps 8 | Quick view

Details

Bentley Brook is a ski in/ski out resort located at the base of Jiminy Peak ski resort. On-site Amenities Include: Heated Indoor/Outdoor Pool (year round), 3 hot tubs, 'Get out & Play ' children's program, 3 tennis courts, game room, exercise equipment, sauna, theater with nightly movies.. At Jiminy - Alpine Slide (…
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

PreviousNext property

$375

4 BR / 3 BA / Sleeps 8

16 Reviews

$375

Inquire

Beautiful Berkshire House w/ Tennis

4 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 16 Reviews

Details

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 …

PreviousNext property

$200

2 BR / 1 BA / Sleeps 4

1 / 10

$200

Book

Berkshire Schoolhouse Cottage

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Welcome to our School House Cottage located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain, this historic home was originally a three room schoolhouse. An addition in the 1960's transformed it into a private home which it remained for many years. Now updated, the cottage has become a …
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Parking
  • Books
  • Pet friendly - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$250

2 BR / 1 BA / Sleeps 5

1 / 14

$250

Book

Lenox Walk to Town / Tanglewood

2 BR / 1 BA / Sleeps 5 | Quick view

Details

This summer cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a beautiful backyard for grilling. There is also an amazing dining room surrounded by windows and the lush forest …
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

PreviousNext property

$120

2 BR / 1 BA / Sleeps 8

1 Reviews

$120

Book

Apartment walking distance to Mass MoCa!!

2 BR / 1 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa!!! Animals are welcome is needed. . The master bedroom has an extended queen sleep number…
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Friendly host ample space

Left on Jul 06, 2014 for a stay in July 2014

Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from noise.

PreviousNext property

$150

1 BR / 2 BA / Sleeps 4

1 / 12

$150

Book

Berkshires Resort Apartment

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

PreviousNext property

$145

1 BR / 1 BA / Sleeps 6

1 Reviews

$145

Book

PanoramicView1000 sq ft Guest Quarters Berkshires

1 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Low long term rates. Call $2500/mo for 3 months. Free Electric Vehicle Charging Station! (240V 40A no J1772) Thanksgiving Special - Nov 24 - Dec 1 - $500 Christmas Special - Dec 20 - Dec 27 - $800 Ski Season Dec 1 - Mar 31 $8000 April $50/nt Summer Cultural May 26, 2014 - Seot 2, 2014 $7500 Summer $200/nt Other $150/…
  • Mountain Views
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

Clean, Comfortable and Convenient

Left on Oct 16, 2014 for a stay in October 2014

This property is perfect for people with pets.

Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels take you to Northwest MA.

PreviousNext property

$150

3 BR / 2 BA / Sleeps 8

1 Reviews

$150

Book

Berkshire's Getaway ---Peace & Tranquility

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

House is very private and located on 4 acres of Land. Back yard is peaceful and overlooks ponds. The backyard has a patio/picnic area with gas grill and firepit. One of the ponds has a spurting and lighted fountain that is relaxing ...so have a campfire at night and watch the lighted fountain for a relaxing evening. …
  • Waterfront
  • Mountain Views
  • Internet Access
  • Fireplace
  • Washing Machine
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(1)

Quaint home on its own lake--don't miss this!

Left on Nov 29, 2014 for a stay in November 2014

The photos speak for themselves. Overall, the home was a great escape from city life, and included its own scenery and lake. My only complaint is that our stay was so short-lived. From our email communication with the owners, they seemed just as charming. We'll be back again.

PreviousNext property

$500

3 BR / 3 BA / Sleeps 8

1 Reviews

$500

Book

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

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 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 …

PreviousNext property

$150

3 BR / 1 BA / Sleeps 5

1 / 9

$150

Book

Hillside Hideaway with Trout Stream

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

PreviousNext property

$43

2 BR / 2 BA / Sleeps 8

1 Reviews

$43

Book

Vacation Village BerkshiresMar20-Apr.3, Only$299WK

2 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Fantastic Value at over 50% off the retail rates! Great Fall Season pricing of only $299 for each entire week's stay! No other fees due! We own this timeshare and can't use it this year! March 20-27th and March 27 to April 3, 2015.-. 2 bedroom, 2 bath, sleeps 6 Fully furnished with cooking utensils, linens and …
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - adapted

Details

Reviews

(1)

Secluded spot, not overly commercialised

Left on Feb 16, 2015 for a stay in September 2014

Didn't go late enough for the Fall Foliage, but even as the leaves were just turning this was a lovely resort to visit. We go to the Highlands of Scotland every other year where the air is so fresh and pure that you want to bottle it. But in this corner of New England we found an environment that nearly matched the Caledonian air!

But in it's favour it is much warmer and the outdoor pool and…

1 2
page 1 of 2
Load more