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Our top choices for West 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 ¥22,844
¥58,769 total
includes taxes & fees
May 13 - May 14
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is ¥16,639
¥22,146 total
includes taxes & fees
May 24 - May 25
All the comforts of home

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, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is ¥27,889
¥65,105 total
includes taxes & fees
Jun 1 - Jun 2
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ¥56,248
¥113,757 total
includes taxes & fees
May 13 - May 14
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 ¥42,163
¥77,198 total
includes taxes & fees
May 13 - May 14
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ¥37,133
¥78,755 total
includes taxes & fees
May 13 - May 14
Cheerful 3-bedroom cottage with woodstove

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is ¥31,728
¥49,616 total
includes taxes & fees
May 13 - May 14
Cozy Riverside Berkshires Retreat

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 ¥25,225
¥84,997 total
includes taxes & fees
May 13 - May 14
Comfortable Berkshires retreat on mtn resort, SISO

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 ¥23,831
¥61,259 total
includes taxes & fees
May 13 - May 14
Near Tanglewood: Historic Summer Retreat

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, (1 review)
"My family and I had a lovely stay at Oscar’s Pond Estate! The house was clean and inviting, and provided everything we needed for a comfortable stay. The surrounding area provided beautiful views as we enjoyed the back deck and yard, complete with a hot tub and fire pit. I highly recommend the nearby Art Omi sculpture park if you stay here. It was a perfect outing for our 2 families with 4 kids ages 2 to 9. The owner was incredibly warm and responsive and provided clear and easy check-in...
United States
Betsy H.
The price is ¥37,447
¥86,688 total
includes taxes & fees
May 13 - May 14
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is ¥23,189
¥80,540 total
includes taxes & fees
May 14 - May 15
Charles Cottage Near Warren St New Renovation

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 ¥27,497
¥65,893 total
includes taxes & fees
May 13 - May 14
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is ¥36,782
¥77,977 total
includes taxes & fees
May 19 - May 20
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

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 ¥43,087
¥89,596 total
includes taxes & fees
May 13 - May 14
Treetop Hideaway in Tyringham

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (27 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is ¥46,221
¥119,010 total
includes taxes & fees
May 13 - May 14
Modern Victorian Walk to Main Street

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, (4 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 ¥88,838
¥208,264 total
includes taxes & fees
May 13 - May 14
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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, (4 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 ¥28,294
¥49,647 total
includes taxes & fees
May 13 - May 14
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is ¥26,792
¥46,327 total
includes taxes & fees
May 13 - May 14
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥7,756
¥44,891 total
includes taxes & fees
May 14 - May 15
Real Estate: Therapy - Lake, Laundry, Love it

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 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.
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
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 West Stockbridge Hotel Reviews

Find out more about West Stockbridge

West Stockbridge Vacation Homes information

Number of reviews
383
Accommodation
464 Vacation Homes
Lowest Price
¥22,146
Highest Price
¥208,264