Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Sep 5 - Sep 7
In two months
Oct 17 - Oct 19
In three months
Nov 14 - Nov 16
In four months
Dec 12 - Dec 14

Browse Select Stockbridge Vacation Homes

Our top choices for Stockbridge vacation homes

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop

Sun Filled Lenox Retreat - Minutes to Tanglewood!

10.0 out of 10, Exceptional, (1)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
The price is CA $316
CA $719 total
includes taxes & fees
Sep 1 - Sep 2
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (255)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is CA $208
CA $310 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

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 CA $225
CA $553 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Smart TV, books

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

9.8 out of 10, Exceptional, (7)
"My wife, two kids, and chocolate lab spent a few days at the cottage to enjoy the snow and hot tub. Everything was set up exactly as described and Nicole was very friendly and proactive. We had a great time and would do it again "
The price is CA $222
CA $546 total
includes taxes & fees
Sep 3 - Sep 4
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Bungalow in the Berkshires
Exterior

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (1)
"Renting this house was very last minute because the place we initially booked fell through - and we're so glad it did! The house was charming, cozy, up-to-date, and beautifully decorated. The neighborhood was nice and quiet, and the drive to downtown was short. I highly recommend this house!"
The price is CA $520
CA $717 total
includes taxes & fees
Aug 24 - Aug 25
Bungalow in the Berkshires
Home in Great Barrington
Fridge, microwave, oven, stovetop

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Our family had a wonderful experience and stay. "
The price is CA $261
CA $420 total
includes taxes & fees
Sep 1 - Sep 2
Home in Great Barrington
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is CA $415
CA $728 total
includes taxes & fees
Sep 12 - Sep 13
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
NEW RENO Historic Creamery in Berkshires w/hot tub
Terrace/patio

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (3)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is CA $294
CA $667 total
includes taxes & fees
Sep 15 - Sep 16
NEW RENO Historic Creamery in Berkshires w/hot tub
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

3-bedroom house in beautiful Berkshires, close to amenities!

The price is CA $265
CA $445 total
includes taxes & fees
Aug 26 - Aug 27
3-bedroom house in beautiful Berkshires, close to amenities!
Perfect House In Hillsdale, Brings Friends & Fam
Exterior

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
The price is CA $258
CA $707 total
includes taxes & fees
Aug 24 - Aug 25
Perfect House In Hillsdale, Brings Friends & Fam
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is CA $223
CA $670 total
includes taxes & fees
Sep 9 - Sep 10
Comfortable Berkshires retreat on mtn resort, SISO
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is CA $329
CA $697 total
includes taxes & fees
Sep 7 - Sep 8
Cheerful 3-bedroom cottage with woodstove
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is CA $760
CA $1,451 total
includes taxes & fees
Aug 25 - Aug 26
Hancock Village Inn at Jiminy Peak
Great Barrington Get Away
Fridge, microwave, oven, stovetop

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 CA $451
CA $790 total
includes taxes & fees
Sep 7 - Sep 8
Great Barrington Get Away
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is CA $342
CA $714 total
includes taxes & fees
Aug 25 - Aug 26
Near Tanglewood: Historic Summer Retreat
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is CA $288
CA $417 total
includes taxes & fees
Sep 1 - Sep 2
Experience Timeless Elegance in The Edith Wharton Room!
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $589
CA $1,106 total
includes taxes & fees
Aug 27 - Aug 28
Spacious 5-bedroom house in charming Lee with WiFi
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Terrace/patio

Historic Berkshires Home Near Tanglewood, Trails & Wineries

9.0 out of 10, Wonderful, (17)
"Of all the properties I have stayed at, this home is my favorite! Excited to be able to stay in a such a historical home in a rich historical area! Amanda was a wonderful host! Provided a comfortable stay. The home had all the necessities! The town has delicious places to eat. Grocery store is great! My hope is to return and spend more time here."
The price is CA $311
CA $663 total
includes taxes & fees
Sep 17 - Sep 18
Historic Berkshires Home Near Tanglewood, Trails & Wineries
The Lakeshore House
Property grounds

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is CA $672
CA $1,112 total
includes taxes & fees
Sep 7 - Sep 8
The Lakeshore House
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is CA $332
CA $473 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Carriage House room with a double bed and private balcony
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

Hotel On North

Hotel On North

10/10 Excellent
"Great surprise in Pittsfield. Very well run. Lovely rooms "
Peter 1-night trip
Posted 1 day ago
Hotel On North