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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (40 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 $651
CA $1,210 total
includes taxes & fees
Sep 28 - Sep 29
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

2. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 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 $286
CA $448 total
includes taxes & fees
Sep 28 - Sep 29
Riverside Retreat in the Berkshires
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

3. 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)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is CA $283
CA $498 total
includes taxes & fees
Oct 11 - Oct 12
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

4. 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)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is CA $99
CA $294 total
includes taxes & fees
Sep 28 - Sep 29
NEW RENO - Chalet-style farm loft near Tanglewood
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is CA $300
CA $469 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
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.

6. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $206
CA $532 total
includes taxes & fees
Sep 28 - Sep 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

7. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is CA $414
CA $835 total
includes taxes & fees
Oct 5 - Oct 6
Spacious Central Berkshires Home for Groups
A spacious living room with a dining area, a kitchen, and a large window.

8. 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 $122
CA $320 total
includes taxes & fees
Sep 28 - Sep 29
1800s Carriage house in Berkshires / Hudson Valley
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (17 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is CA $227
CA $558 total
includes taxes & fees
Sep 29 - Sep 30
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

10. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is CA $400
CA $806 total
includes taxes & fees
Oct 28 - Oct 29
Treetop Hideaway in Tyringham
A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is CA $445
CA $984 total
includes taxes & fees
Oct 4 - Oct 5
Ellie’s Overlook, best view 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.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"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 $137
CA $483 total
includes taxes & fees
Oct 5 - Oct 6
Real Estate: Therapy - Lake, Laundry, Love it
A camping setup with a metal chair and a table by a river in a forest.

13. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is CA $283
CA $486 total
includes taxes & fees
Sep 28 - Sep 29
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A white two-story house with a porch, surrounded by trees and a hill.

14. 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 $280
CA $669 total
includes taxes & fees
Sep 30 - Oct 1
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

15. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is CA $719
CA $1,235 total
includes taxes & fees
Oct 18 - Oct 19
Stylish Mid-century Modern Berkshires Cape
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is CA $566
CA $994 total
includes taxes & fees
Sep 28 - Sep 29
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A modern building with a wooden deck and a door.

17. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is CA $327
CA $822 total
includes taxes & fees
Sep 28 - Sep 29
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is CA $249
CA $804 total
includes taxes & fees
Oct 5 - Oct 6
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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.

19. 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, (8 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 $686
CA $1,701 total
includes taxes & fees
Oct 28 - Oct 29
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

20. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is CA $263
CA $626 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any of the amenities that they charge extra for, but because I was traveling, it was nice to just have a quiet night in."
Rachel Elion 1-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
248
Accommodation
411 Vacation Homes
Lowest Price
CA $294
Highest Price
CA $1,701

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