We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Stockbridge, MA and nearby

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 49 Rentals in the Stockbridge Area
loading...
From
$571
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Private Fishing Lake/River, Satellite TV & more
32 photos Details Reviews (1) Make Enquiry
From
$113
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Grill, Safe, Mountain Views & more
19 photos Details Reviews (21) Make Enquiry
From
$229
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Dishwasher, Dryer, Internet Access & more
16 photos Details Reviews (4) Make Enquiry
From
$229
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Fireplace, Washer, Internet Access & more
11 photos Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 31 July 2014
Nice house but tired bathrooms and kitchen. One great bedroom, two so so. Hot one nite and needed non existing a/c. Great screened porch with view of water. Canoe was a plus...
See all reviews
From
$245
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details Make Enquiry
From
$658
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
5 photos Details Make Enquiry
From
$572
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Satellite TV, Dishwasher, Air Conditioning & more
23 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Washer, Air Conditioning, Grill & more
13 photos Details Make Enquiry
From
$149
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Grill, Garden, Satellite TV & more
16 photos Details Make Enquiry
From
$229
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Dishwasher, Grill, Washer & more
24 photos Details Make Enquiry
Get the List

The following rentals are within 10 kilometres of Stockbridge, Massachusetts.

From
$286
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Washer, Mountain Views, Dishwasher & more
10 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 21 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...
See all reviews
From
$400
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Internet Access, Dryer, Washer & more
17 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 13 June 2014
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...
See all reviews
From
$343
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 5
Fireplace, Satellite TV, Washer & more
25 photos Details Reviews (2) Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Internet Access, Grill, Washer & more
11 photos Details Reviews (2) Make Enquiry
4 of 5 stars Reviewed 18 June 2013
This property was a great home base for our brief visit to the Berkshires. Plenty of space and well equipped. We especially enjoyed the beautiful property, whether sitting on the...
See all reviews
From
$172
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
4 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 June 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...
See all reviews
From
$143
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Satellite TV, Internet Access, Washer & more
6 photos Details Reviews (2) Make Enquiry
5 of 5 stars Reviewed 19 December 2013
We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
See all reviews
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Mountain Views, Fireplace, Grill & more
8 photos Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 June 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...
See all reviews
From
$429
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 11
Bookings
Dryer, Grill, Internet Access & more
33 photos Details Reviews (8) Make Enquiry
4 of 5 stars Reviewed 28 September 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 3 September 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...
See all reviews
From
$286
Per Night
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
Dryer, Garden, Washer & more
12 photos Details Reviews (7) Make Enquiry
5 of 5 stars Reviewed 1 September 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 31 August 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...
See all reviews
From
$286
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Private Fishing Lake/River, Dishwasher, Washer & more
14 photos Details Reviews (4) Make Enquiry
5 of 5 stars Reviewed 26 August 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 26 August 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...
See all reviews
From
$658
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Air Conditioning, Balcony, Internet Access & more
33 photos Details Reviews (3) Make Enquiry
From
$172
Per Night
4 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Washer, Dryer, Grill & more
21 photos Details Reviews (16) Make Enquiry
5 of 5 stars Reviewed 6 September 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 10 February 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...
See all reviews
From
$223
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Pool, Satellite TV, Internet Access & more
10 photos Details Reviews (9) Make Enquiry
5 of 5 stars Reviewed 18 August 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 23 July 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...
See all reviews
From
$372
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Dishwasher, Safe, Air Conditioning & more
27 photos Details Reviews (1) Make Enquiry
3 of 5 stars Reviewed 12 September 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...
See all reviews
From
$200
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
4 photos Details Make Enquiry
From
$286
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Washer, Grill, Fireplace & more
7 photos Details Make Enquiry
From
$5,148
Per Week
6 Bedrooms, 6 Bathrooms, Sleeps 12
Shared Outdoor Pool (Heated), Mountain Views & more
25 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Housekeeping Optional, Mountain Views, Dishwasher & more
12 photos Details Make Enquiry
From
$400
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 10
Mountain Views, Fireplace, Internet Access & more
9 photos Details Make Enquiry
From
$114
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Shared Indoor Pool, Balcony, Housekeeping Optional & more
12 photos Details Make Enquiry
From
$257
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Satellite TV, Dryer, Garden & more
19 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Washer, Air Conditioning, Internet Access & more
19 photos Details Make Enquiry
From
$458
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Private Indoor Pool, Water Views & more
24 photos Details Make Enquiry
From
$277
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Internet Access, Air Conditioning, Dishwasher & more
15 photos Details Make Enquiry
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Air Conditioning, Internet Access, Grill & more
12 photos Details Make Enquiry
From
$858
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 12
7 photos Details Make Enquiry
From
$229
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Garden, Housekeeping Optional, Air Conditioning & more
10 photos Details Make Enquiry
From
$543
Per Night
4 Bedrooms, 6 Bathrooms, Sleeps 12
Internet Access, Grill, Fireplace & more
22 photos Details Make Enquiry
From
$343
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Fireplace, Washer, Grill & more
11 photos Details Make Enquiry
From
$229
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Dishwasher, Washer, Internet Access & more
10 photos Details Make Enquiry
From
$429
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Shared Indoor Pool, Satellite TV, Sauna & more
5 photos Details Make Enquiry
From
$343
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Garden, Dryer, Satellite TV & more
9 photos Details Make Enquiry
From
$143
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Internet Access, Balcony, Garden & more
10 photos Details Make Enquiry
From
$229
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Booking
7 photos Details Make Enquiry
From
$200
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
2 photos Details Make Enquiry
From
$286
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Washer, Internet Access, Housekeeping Optional & more
10 photos Details Make Enquiry
From
$215
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 10
Private Fishing Lake/River, Satellite TV, Fireplace & more
12 photos Details Make Enquiry
From
$229
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
Private Outdoor Pool (Unheated), Garden, Washer & more
15 photos Details Make Enquiry
From
$343
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Air Conditioning, Fireplace, Internet Access & more
23 photos Details Make Enquiry
Go to map view
Book Online(43)
Use filters to find the best results!

Suitability

  • Wheelchair access (6)
  • Elder access (23)
  • Suitable for children (33)
  • Pet friendly (15)
  • Smoking allowed (0)

Amenities

  • Internet (42)
  • Other outdoor space (38)
  • Grill (37)
  • Parking (35)
  • Washer/Dryer (34)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities