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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Stockbridge holiday homes

A staircase with a wooden handrail and a white wall with a light switch.

1. 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 HK$1,377
HK$2,213 total
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

2. 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 HK$2,974
HK$5,452 total
includes taxes & fees
11 Nov - 12 Nov
Secluded Family Home in Serene Stockbridge Woods
A dining area with a wooden table, black chairs, and a vase with green plants.

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 HK$1,569
HK$2,735 total
includes taxes & fees
25 Oct - 26 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A modern bedroom with a loft bed, a small desk, and a window with a view of trees.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is HK$1,695
HK$2,648 total
includes taxes & fees
3 Nov - 4 Nov
Home in Great Barrington
A modern living room with a sofa, armchair, coffee table, and TV.

5. 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 HK$2,295
HK$4,711 total
includes taxes & fees
1 Nov - 2 Nov
Spacious Central Berkshires Home for Groups
A living room with a sofa, armchairs, a coffee table, and a television.

6. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 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 HK$2,493
HK$4,985 total
includes taxes & fees
26 Oct - 27 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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.

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

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is HK$2,472
HK$5,423 total
includes taxes & fees
27 Oct - 28 Oct
Ellie’s Overlook, best view in the Berkshires!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

8. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 HK$2,103
HK$4,404 total
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is HK$3,139
HK$5,513 total
includes taxes & fees
17 Nov - 18 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 HK$549
HK$1,632 total
includes taxes & fees
27 Oct - 28 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A spacious living room with a dining area, a kitchen, and a large window.

11. 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 HK$667
HK$1,750 total
includes taxes & fees
17 Nov - 18 Nov
1800s Carriage house in Berkshires / Hudson Valley
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.

12. 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 HK$1,144
HK$2,952 total
includes taxes & fees
26 Oct - 27 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A bedroom with a bed, a nightstand, a lamp, a chair, and a dresser.

13. Mayas Shangrila

Mayas Shangrila
2.0 star property
Richmond
The price is HK$6,373
HK$9,101 total
includes taxes & fees
30 Oct - 31 Oct
Mayas Shangrila
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.

14. 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, (9 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 HK$4,442
HK$10,422 total
includes taxes & fees
29 Oct - 30 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

15. 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, (16 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 HK$1,569
HK$2,698 total
includes taxes & fees
26 Oct - 27 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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 HK$1,257
HK$3,087 total
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

17. 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 HK$502
HK$2,393 total
includes taxes & fees
28 Oct - 29 Oct
Real Estate: Therapy - Lake, Laundry, Love it
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 HK$1,546
HK$3,651 total
includes taxes & fees
18 Nov - 19 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A cozy living room with a sofa, a fireplace, and large windows.

19. 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 HK$3,002
HK$5,331 total
includes taxes & fees
27 Oct - 28 Oct
Luxury Barn Near Hudson With New Private Sauna
A forested area with a grassy clearing.

20. Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires

Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
Richmond
The price is HK$7,059
HK$9,852 total
includes taxes & fees
24 Oct - 25 Oct
Mayas Shangrila - Historic 200-Year-Old Farmhouse on 4 Secluded Acres in the Berkshires
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 Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"nice room"
RICHARD 1-night trip
Posted less than an hour ago
Quality Inn Lee - Lenox South

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
160
Accommodation
424 Vacation Homes
Lowest Price
HK$1,632
Highest Price
HK$10,422

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