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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Stockbridge

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is SAR 547
SAR 1,411 total
includes taxes & fees
2 Dec - 3 Dec
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"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."
United States
James D.
The price is SAR 601
SAR 1,480 total
includes taxes & fees
2 Dec - 3 Dec
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
The price is SAR 608
SAR 1,018 total
includes taxes & fees
15 Dec - 16 Dec
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in Housatonic

10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is SAR 506
SAR 909 total
includes taxes & fees
4 Dec - 5 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Vacation Home in Hillsdale

8.4 out of 10, Very Good, (5)
"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. "
United States
Stefanie K.
The price is SAR 698
SAR 1,963 total
includes taxes & fees
6 Dec - 7 Dec
Perfect House In Hillsdale, Brings Friends & Fam
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Vacation Home in Pittsfield

2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is SAR 1,010
SAR 1,853 total
includes taxes & fees
3 Dec - 4 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is SAR 889
SAR 1,886 total
includes taxes & fees
8 Dec - 9 Dec
Cheerful 3-bedroom cottage with woodstove
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is SAR 506
SAR 1,395 total
includes taxes & fees
2 Dec - 3 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is SAR 760
SAR 1,117 total
includes taxes & fees
2 Dec - 3 Dec
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is SAR 1,069
SAR 1,965 total
includes taxes & fees
2 Dec - 3 Dec
Great Barrington Get Away
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

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!"
United States
Roberta
The price is SAR 2,124
SAR 4,983 total
includes taxes & fees
2 Dec - 3 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Vacation Home in Valatie

10.0 out of 10, Exceptional, (57)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
The price is SAR 1,013
SAR 2,017 total
includes taxes & fees
2 Dec - 3 Dec
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Vacation Home in Hancock

9.8 out of 10, Exceptional, (72)
"Great communication. Lots of games for the kids. Comfortable beds. Great living and game room. "
United States
Samuel R.
The price is SAR 990
SAR 2,053 total
includes taxes & fees
2 Dec - 3 Dec
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is SAR 1,594
SAR 2,992 total
includes taxes & fees
8 Dec - 9 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Interior
Artists’ Hideaway in Old Chatham

Vacation Home in Old Chatham

The price is SAR 716
SAR 1,770 total
includes taxes & fees
2 Dec - 3 Dec
Artists’ Hideaway in Old Chatham
Exterior
Hancock Village Inn Near Jiminy Peak

Vacation Home in Hancock

10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is SAR 2,060
SAR 3,753 total
includes taxes & fees
2 Dec - 3 Dec
Hancock Village Inn Near Jiminy Peak
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Vacation Home in Hancock

9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is SAR 1,208
SAR 2,748 total
includes taxes & fees
2 Dec - 3 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Property grounds
The Lakeshore House

Vacation Home in Niverville

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
The price is SAR 1,820
SAR 3,009 total
includes taxes & fees
2 Dec - 3 Dec
The Lakeshore House
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

Quality Inn

10/10 Excellent
"clean warm room. breakfast was small but good enough to start the day. coffee was delicious. quiet which was nice and also very close to the town center with shops so that was convenient "
Gisselle 2-night trip
Posted 23 hours ago
Quality Inn

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