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Stockbridge Vacation Rentals

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Our top choices for Stockbridge vacation homes

1. Hudson Valley Multi-Unit Escape: Secluded + Scenic

Hudson Valley Multi-Unit Escape: Secluded + Scenic
Claverack
The price is CA $418
CA $1,451 total
includes taxes & fees
Aug 21 - Aug 22
Hudson Valley Multi-Unit Escape: Secluded + Scenic

2. Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood
New Lebanon
Berkshires Mountain Retreat w Panoramic Views, 5 Decks, Hot Tub, near Tanglewood

3. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (21 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 CA $324
CA $495 total
includes taxes & fees
Aug 17 - Aug 18
Cozy Riverside Berkshires Retreat

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 CA $303
CA $637 total
includes taxes & fees
Aug 12 - Aug 13
stylish Berkshires Retreat

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (35 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is CA $378
CA $573 total
includes taxes & fees
Aug 12 - Aug 13
Home in Great Barrington

6. 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 $128
CA $325 total
includes taxes & fees
Aug 3 - Aug 4
NEW RENO - Chalet-style farm loft near Tanglewood

7. 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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is CA $300
CA $648 total
includes taxes & fees
Aug 25 - Aug 26
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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 CA $284
CA $628 total
includes taxes & fees
Aug 12 - Aug 13
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

9. 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 $167
CA $368 total
includes taxes & fees
Aug 5 - Aug 6
1800s Carriage house in Berkshires / Hudson Valley

10. 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 CA $350
CA $571 total
includes taxes & fees
Aug 24 - Aug 25
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

11. 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 $472
CA $902 total
includes taxes & fees
Aug 31 - Sep 1
Treetop Hideaway in Tyringham

12. 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 CA $246
CA $796 total
includes taxes & fees
Aug 4 - Aug 5
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

13. 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 CA $501
CA $943 total
includes taxes & fees
Aug 31 - Sep 1
Spacious Central Berkshires Home for Groups

14. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (4 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 $421
CA $831 total
includes taxes & fees
Aug 4 - Aug 5
1789 Shaker Farmhouse in Berkshires/Hudson Valley

15. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is CA $225
CA $761 total
includes taxes & fees
Aug 2 - Aug 3
Comfortable Berkshires retreat on mtn resort, SISO

16. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is CA $440
CA $773 total
includes taxes & fees
Aug 2 - Aug 3
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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, (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 CA $793
CA $1,824 total
includes taxes & fees
Aug 6 - Aug 7
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

18. 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.
The price is CA $866
CA $1,552 total
includes taxes & fees
Aug 9 - Aug 10
Berkshire House Stay: 5BR/5BA

19. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature
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

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
260
Accommodation
434 Vacation Homes
Lowest Price
CA $325
Highest Price
CA $1,824

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