Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge and around

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"We enjoyed our stay. Excellent location to explore Western Mass!"
The price is €200
includes taxes & fees
28 Oct - 29 Oct
Berkshire Village Carriage House - Super Private!!

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is €342
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
The price is €336
includes taxes & fees
6 Oct - 7 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sun Filled Lenox Retreat - Minutes to Tanglewood!

9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
The price is €436
includes taxes & fees
6 Oct - 7 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is €230
includes taxes & fees
3 Nov - 4 Nov
Home in Great Barrington

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (2)
"Great location, very clean and well appointed with everyth"
The price is €364
includes taxes & fees
13 Oct - 14 Oct
Bungalow in the Berkshires

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (4)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is €412
includes taxes & fees
6 Oct - 7 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub

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

2.0 star property
8.0 out of 10, Very good, (5)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is €463
includes taxes & fees
4 Nov - 5 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €438
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is €414
includes taxes & fees
6 Oct - 7 Oct
Comfortable Berkshires retreat on mtn resort, SISO

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

10.0 out of 10, Exceptional, (1)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
The price is €277
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is €971
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak

Cozy. Clean. Free bagel shop.

10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
The price is €580
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
The price is €366
includes taxes & fees
7 Oct - 8 Oct
Near Tanglewood: Historic Summer Retreat

Experience Timeless Elegance in The Edith Wharton Room!

The price is €259
includes taxes & fees
28 Oct - 29 Oct
Experience Timeless Elegance in The Edith Wharton Room!

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

10.0 out of 10, Exceptional, (1)
"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!"
The price is €1,230
includes taxes & fees
13 Oct - 14 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is €453
includes taxes & fees
3 Nov - 4 Nov
Great Barrington Get Away

Spacious 5-bedroom house in charming Lee with WiFi

The price is €716
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is €699
includes taxes & fees
6 Oct - 7 Oct
The Lakeshore House

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
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

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
11,506
Accommodation
429 Holiday Homes
Lowest Price
€71
Highest Price
€319

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