A river surrounded by autumn-colored trees and a forested hill.

Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Stockbridge vacation homes

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

1. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is CA $643
CA $1,099 total
includes taxes & fees
Nov 23 - Nov 24
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A dining area with a wooden table, chairs, and a ceiling fan.

2. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is CA $283
CA $421 total
includes taxes & fees
Nov 2 - Nov 3
Leaf-Peeper Paradise in the Berkshires
A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

3. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is CA $1,084
CA $1,825 total
includes taxes & fees
Nov 9 - Nov 10
Beautiful and Private Home Centrally Located in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

4. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is CA $477
CA $904 total
includes taxes & fees
Nov 2 - Nov 3
Secluded Family Home in Serene Stockbridge Woods
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

5. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is CA $280
CA $492 total
includes taxes & fees
Nov 1 - Nov 2
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern living room with a sofa, armchair, coffee table, and TV.

6. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is CA $409
CA $839 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Central Berkshires Home for Groups
A living room with a sofa, armchairs, a coffee table, and a television.

7. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is CA $444
CA $888 total
includes taxes & fees
Oct 31 - Nov 1
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

8. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is CA $302
CA $475 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

9. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is CA $440
CA $942 total
includes taxes & fees
Nov 5 - Nov 6
Ellie’s Overlook, best view in the Berkshires!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

10. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is CA $98
CA $283 total
includes taxes & fees
Nov 1 - Nov 2
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

11. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is CA $375
CA $791 total
includes taxes & fees
Nov 16 - Nov 17
Treetop Hideaway in Tyringham
A spacious living room with a dining area, a kitchen, and a large window.

12. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is CA $119
CA $310 total
includes taxes & fees
Nov 5 - Nov 6
1800s Carriage house in Berkshires / Hudson Valley
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

13. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (5 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is CA $559
CA $982 total
includes taxes & fees
Nov 16 - Nov 17
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $204
CA $529 total
includes taxes & fees
Nov 5 - Nov 6
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

15. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is CA $76
CA $409 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A hot tub with a string of lights above it, set against a dark night sky.

16. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $224
CA $555 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

17. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is CA $791
CA $1,829 total
includes taxes & fees
Oct 31 - Nov 1
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A white two-story house with a porch, surrounded by trees and a hill.

18. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is CA $246
CA $626 total
includes taxes & fees
Nov 1 - Nov 2
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A room with a large window, two sofas, and a small table.

19. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is CA $1,260
CA $1,758 total
includes taxes & fees
Nov 3 - Nov 4
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
A cozy living room with a sofa, a fireplace, and large windows.

20. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is CA $535
CA $962 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Barn Near Hudson With New Private Sauna
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I booked this for one of my bus drivers & he told me he had a good time theree in the hotel. Clean & quiet."
Smath 1-night trip
Posted 2 hours ago
Quality Inn Great Barrington

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
190
Accommodation
427 Vacation Homes
Lowest Price
CA $283
Highest Price
CA $1,829

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