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Our top choices for Stockbridge vacation homes

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 ¥26,688
¥64,545 total
includes taxes & fees
Jun 22 - Jun 23
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥14,715
¥53,858 total
includes taxes & fees
Jun 22 - Jun 23
Real Estate: Therapy - Lake, Laundry, Love it

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ¥25,678
¥63,058 total
includes taxes & fees
Jun 9 - Jun 10
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is ¥32,459
¥50,759 total
includes taxes & fees
Jun 9 - Jun 10
Cozy Riverside Berkshires Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is ¥23,226
¥61,202 total
includes taxes & fees
Jun 9 - Jun 10
Near Tanglewood: Historic Summer Retreat

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is ¥25,534
¥60,213 total
includes taxes & fees
Jun 15 - Jun 16
stylish Berkshires Retreat

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ¥28,051
¥89,588 total
includes taxes & fees
Jun 9 - Jun 10
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is ¥38,229
¥58,458 total
includes taxes & fees
Jun 14 - Jun 15
Home in Great Barrington

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is ¥32,058
¥54,755 total
includes taxes & fees
Jun 15 - Jun 16
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is ¥25,678
¥64,306 total
includes taxes & fees
Jun 9 - Jun 10
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is ¥46,164
¥93,863 total
includes taxes & fees
Jun 9 - Jun 10
Treetop Hideaway in Tyringham

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very Good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is ¥27,410
¥66,963 total
includes taxes & fees
Jun 10 - Jun 11
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥37,989
¥80,929 total
includes taxes & fees
Jun 9 - Jun 10
Cheerful 3-bedroom cottage with woodstove

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is ¥25,807
¥87,136 total
includes taxes & fees
Jun 9 - Jun 10
Comfortable Berkshires retreat on mtn resort, SISO

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is ¥39,111
¥89,763 total
includes taxes & fees
Jun 11 - Jun 12
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

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
7.8 out of 10, Good, (7 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 ¥50,347
¥88,466 total
includes taxes & fees
Jun 9 - Jun 10
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (1 review)
"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 ¥48,087
¥85,404 total
includes taxes & fees
Jun 9 - Jun 10
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Family Cabin w/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes

Family Cabin w/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes
Otis
10.0 out of 10, Exceptional, (1 review)
"I wish I could give The Owl and Firefly ten stars instead of 5. It's truly such a special vacation place that’s bound to bring joy to any family who comes here! Incredibly beautiful and so carefully planned and equipped, with great attention and much generosity given to every single detail, it made us feel so comfortable and truly cared for in a way I've never felt before in a vacation rental. The photos are very accurate but everything is even better when you can stand in the middle of the...
United States
Karen C.
Family Cabin w/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is ¥76,138
¥138,044 total
includes taxes & fees
Jun 22 - Jun 23
Spacious 5-bedroom house in charming Lee with WiFi

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is ¥38,085
¥82,647 total
includes taxes & fees
Jun 9 - Jun 10
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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
250
Accommodation
416 Vacation Homes
Lowest Price
¥50,759
Highest Price
¥138,044