Holiday Homes in West Stockbridge

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Featured Holiday Homes in West Stockbridge

Our top choices for West Stockbridge holiday homes

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 NZ$875
includes taxes & fees
4 Sept - 5 Sept
Sun Filled Lenox Retreat - Minutes to Tanglewood!

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 NZ$379
includes taxes & fees
16 Sept - 17 Sept
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 NZ$673
includes taxes & fees
1 Sept - 2 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

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

9.8 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 NZ$664
includes taxes & fees
1 Sept - 2 Sept
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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 NZ$892
includes taxes & fees
11 Sept - 12 Sept
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

All the comforts of home

9.0 out of 10, Wonderful, (24)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is NZ$239
includes taxes & fees
1 Sept - 2 Sept
All the comforts of home

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Our family had a wonderful experience and stay. "
The price is NZ$514
includes taxes & fees
1 Sept - 2 Sept
Home in Great Barrington

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is NZ$822
includes taxes & fees
17 Sept - 18 Sept
Comfortable Berkshires retreat on mtn resort, SISO

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 NZ$865
includes taxes & fees
25 Aug - 26 Aug
Perfect House In Hillsdale, Brings Friends & Fam

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 NZ$849
includes taxes & fees
3 Sept - 4 Sept
Cheerful 3-bedroom cottage with woodstove

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 NZ$873
includes taxes & fees
24 Aug - 25 Aug
Bungalow in the Berkshires

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 NZ$805
includes taxes & fees
21 Aug - 22 Aug
NEW RENO Historic Creamery in Berkshires w/hot tub

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 NZ$864
includes taxes & fees
21 Aug - 22 Aug
Near Tanglewood: Historic Summer Retreat

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

The price is NZ$534
includes taxes & fees
15 Sept - 16 Sept
3-bedroom house in beautiful Berkshires, close to amenities!

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 NZ$878
includes taxes & fees
7 Sept - 8 Sept
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is NZ$966
includes taxes & fees
2 Sept - 3 Sept
Great Barrington Get Away

Experience Timeless Elegance in The Edith Wharton Room!

The price is NZ$508
includes taxes & fees
1 Sept - 2 Sept
Experience Timeless Elegance in The Edith Wharton Room!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is NZ$1,870
includes taxes & fees
8 Sept - 9 Sept
Hancock Village Inn at Jiminy Peak

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,347
includes taxes & fees
26 Aug - 27 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson

9.6 out of 10, Exceptional, (8)
"Great space for our family of four and dog. Lots of room to spread out and relax. Nice local events going on and great location to stores and short drive to hiking spots and many restaurants. Host had great communication with us and answered all of our questions in a really timely manner. Definitely recommend this spot!"
The price is NZ$963
includes taxes & fees
3 Sept - 4 Sept
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
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