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Resorts and apartments in Berkshires, MA

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All 103 Rentals in Berkshires
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From
$500
Per Night
Sheffield
4 Bedrooms, 3 Bathrooms, Sleeps 15
19 photos Details Reviews (8) Make Inquiry
From
$350
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
17 photos Details Reviews (1) Make Inquiry
From
$115
Per Night
Charlemont
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
35 photos Details Reviews (97) Make Inquiry
Also consider
Great value in Gt Barrington- 1 week in the summer
2 Bedrooms, sleeps 4
$200 / night
New England in October
1 Bedroom, sleeps 4
$125 / night
The Cottage B&B near Tanglewood in The Berkshires
3 Bedrooms, sleeps 6
$99 - $249 / night
Lovely Cottage Minutes to Tanglewood -Walk to Town
3 Bedrooms, sleeps 6
$250 - $300 / night
From
$160
Per Night
North Egremont
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
35 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed September 11, 2014
I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
5 of 5 stars Reviewed September 4, 2014
Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
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From
$275
Per Night
Becket
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
32 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 29, 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...
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From
$499
Per Night
Stockbridge
4 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
32 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 18, 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...
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From
$150
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
4 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 17, 2014
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...
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From
$200
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
8 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed June 17, 2014
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...
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From
$375
Per Night
Lee
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
33 photos Details Reviews (8) Make Inquiry
4 of 5 stars Reviewed September 27, 2014
We went there for a golf buddy trip and it was the perfect place for us in the Berkshires. Place was very clean, and had all the comforts of home. Robin is super friendly and...
5 of 5 stars Reviewed September 3, 2014
This is a wonderful home! Robin has taken care with the furnishing and finishings, which are a nice blend of antique and modern. Her love of the home and region is apparent...
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From
$20
Per Night
North Adams
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
10 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 6, 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...
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From
$250
Per Night
West Stockbridge
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
12 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed August 31, 2014
We were a group nine. We found the house to have a rustic charm complete with hardwood floors and exposed beams in the walls and ceilings. We tended to congregate in the living...
5 of 5 stars Reviewed August 30, 2014
My brother and sister and I, along with our significant others, gathered together here for a week to enjoy the Berkshires. The house suited our needs much better than other...
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From
$300
Per Night
Lee
3 Bedrooms, 2 Bathrooms, Sleeps 5
25 photos Details Reviews (2) Make Inquiry
From
$229
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
4 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed August 11, 2013
Aside from the excessive amount of men's shirts in the closets (closets and drawers had not been emptied so storage space was minimal), the full trash bins and dirty dishes...
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From
$250
Per Night
West Stockbridge
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
14 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 25, 2014
We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
5 of 5 stars Reviewed August 25, 2014
Four of us stayed for a week, mostly cooking in, aided by a well-equipped kitchen and outdoor grill, as well as very comfortable dining areas - inside and out. Nice yard with...
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From
$150
Per Night
Lenox
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
21 photos Details Reviews (16) Make Inquiry
5 of 5 stars Reviewed September 5, 2014
Spent a late summer weekend with my grown children and their friends. The Gartner House had plenty of room for us to relax and spread out. The rooms were old but charming and...
4 of 5 stars Reviewed February 9, 2014
We stayed at the Gartner House in the middle of winter. The house is comfy and well appointed. The kitchen has every thing you would need. The record player and variety of records...
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From
$285
Per Night
North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed August 24, 2014
I booked the Rose & Goat Retreat for my sister's Bachelorette Weekend in the Berkshires! Not only was it the perfect location because it was only 11 miles away from our zip lining...
5 of 5 stars Reviewed March 13, 2014
This place is an absolutely gorgeous lodge, with an incredible view of the Berkshires. Margo was very hospitable and took great care of all of our needs. The pictures don't do...
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From
$195
Per Night
Great Barrington
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
10 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed August 17, 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed July 22, 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
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From
$200
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
16 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed October 24, 2013
Some friends and I wanted to have a reunion as we are spread out along the east coast, and we were debating between camping or renting. I heard no end of the gratitude from my...
5 of 5 stars Reviewed September 30, 2013
We rented this cabin originally for 5: 2 adults and 3 children (6,11,13). At the last minute our older daughter (18) decided to join us. The cabin is very spacious and...
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From
$250
Per Night
North Adams
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 16, 2014
The cottage is well located, seemingly remote, but with nearby access to local attractions and restaurants. I enjoyed sitting on the deck, looking out over the water in the...
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From
$200
Per Night
Stockbridge
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
11 photos Details Reviews (1) Make Inquiry
3 of 5 stars Reviewed July 30, 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...
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From
$250
Per Night
Granville
5 Bedrooms, 3 Bathrooms, Sleeps 12
Booking
5 photos Details Make Inquiry
From
$300
Per Night
Great Barrington
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
11 photos Details Make Inquiry
From
$225
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
11 photos Details Make Inquiry
From
$4,500
Per Week
Great Barrington
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details Make Inquiry
From
$179
Per Night
Hancock
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
16 photos Details Make Inquiry
From
$171
Per Night
Pittsfield
3 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details Make Inquiry
From
$300
Per Night
Monterey
4 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details Make Inquiry
From
$125
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
10 photos Details Make Inquiry
From
$100
Per Night
South Lee
1 Bedroom, 2 Bathrooms, Sleeps 4
12 photos Details Make Inquiry
From
$400
Per Night
Lenox
4 Bedrooms, 2 Bathrooms, Sleeps 10
24 photos Details Make Inquiry
From
$200
Per Night
Great Barrington
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
10 photos Details Make Inquiry
From
$242
Per Night
Lenox
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details Make Inquiry
From
$130
Per Night
Pittsfield
3 Bedrooms, 1 Bathroom, Sleeps 8
20 photos Details Make Inquiry
From
$130
Per Night
Stockbridge
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details Make Inquiry
From
$375
Per Night
Lee
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details Make Inquiry
From
$300
Per Night
Great Barrington
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details Make Inquiry
From
$200
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details Make Inquiry
From
$134
Per Night
Hancock
3 Bedrooms, 2 Bathrooms, Sleeps 8
13 photos Details Make Inquiry
From
$200
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
7 photos Details Make Inquiry
From
$175
Per Night
Lee
1 Bedroom, 1 Bathroom, Sleeps 2
2 photos Details Make Inquiry
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Suitability

  • Wheelchair access (12)
  • Elder access (47)
  • Suitable for children (73)
  • Pet friendly (31)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (77)
  • Internet (75)
  • Parking (67)
  • Washer/Dryer (63)
  • Grill (62)
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Book Online(85)

Suitability

  • Wheelchair access (12)
  • Elder access (47)
  • Suitable for children (73)
  • Pet friendly (31)
  • Smoking allowed (0)

Amenities

  • Other outdoor space (77)
  • Internet (75)
  • Parking (67)
  • Washer/Dryer (63)
  • Grill (62)
  • View all amenities