A nighttime view of a residential area with houses adorned with holiday lights.

Holiday Homes in Stockbridge

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Stockbridge holiday homes

Outdoor dining

1. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is AU$879
includes taxes & fees
30 Aug - 31 Aug
Stockbridge In-town Escape
Interior

2. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is AU$430
includes taxes & fees
7 Sept - 8 Sept
Cozy Riverside Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

3. 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 AU$330
includes taxes & fees
13 Aug - 14 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
Smart TV

4. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AU$593
includes taxes & fees
8 Sept - 9 Sept
stylish Berkshires Retreat
Coffee/tea maker, fridge, microwave, oven

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (37 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is AU$568
includes taxes & fees
12 Aug - 13 Aug
Home in Great Barrington
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (9 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 AU$442
includes taxes & fees
1 Sept - 2 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is AU$506
includes taxes & fees
26 Aug - 27 Aug
Real Estate: Therapy - Lake, Laundry, Love it
Outdoor spa tub

8. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$586
includes taxes & fees
9 Sept - 10 Sept
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

9. 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, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$568
includes taxes & fees
9 Sept - 10 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV, DVD player, books, video library

10. 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 AU$356
includes taxes & fees
9 Sept - 10 Sept
1800s Carriage house in Berkshires / Hudson Valley
Smart TV, books

11. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is AU$852
includes taxes & fees
19 Aug - 20 Aug
Spacious Central Berkshires Home for Groups
4 bedrooms, travel cot, WiFi, bed sheets

12. 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 AU$1,204
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
TV

13. 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 AU$871
includes taxes & fees
2 Sept - 3 Sept
Treetop Hideaway in Tyringham
Coffee/tea maker, fridge, microwave, stovetop

14. 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, (6 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AU$805
includes taxes & fees
11 Aug - 12 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
TV, fireplace, printers

15. 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, (7 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 AU$1,845
includes taxes & fees
13 Aug - 14 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Exterior

16. 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 AU$761
includes taxes & fees
1 Sept - 2 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 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 AU$937
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (10 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is AU$562
includes taxes & fees
10 Aug - 11 Aug
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Coffee/tea maker, fridge, microwave, stovetop

19. Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
Berkshire House Stay: 5BR/5BA
TV, fireplace, DVD player, books

20. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is AU$1,076
includes taxes & fees
21 Aug - 22 Aug
Mtn-View Retreat in Huson Valley: Great for Groups
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The staff were friendly, helpful with finding restaurants and other local attractions. Our room was immaculate and nicely furnished with modern furnishings in great condition. The room was quiet--we never heard our neighbors. It was pleasant to sit on the balcony and read. The location is great, 15 or 20 mins to Tanglewood depending on time. A very nice breakfast with lots of choices. We would definitely recommend this Inn to friends, and plan to return for future trips to Tanglewood and The Berkshires. ."
John 2-night trip
Posted 8 hours ago
The Yankee Inn

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
128
Accommodation
434 Holiday Homes
Lowest Price
AU$330
Highest Price
AU$1,845