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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Vacation Homes in West Stockbridge

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 SAR 1,054
SAR 2,054 total
includes taxes & fees
7 Sep - 8 Sep
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 SAR 1,040
SAR 2,029 total
includes taxes & fees
28 Aug - 29 Aug
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
All the comforts of home
Property grounds

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 SAR 399
SAR 530 total
includes taxes & fees
17 Aug - 18 Aug
All the comforts of home
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 SAR 1,122
SAR 1,978 total
includes taxes & fees
14 Sep - 15 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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. "
Home in Great Barrington
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
Property grounds

Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.

10.0 out of 10, Exceptional, (4)
"The property was spacious and very comfortable, had everything we needed. The area was also nice and fun to explore. "
The price is SAR 1,257
SAR 2,071 total
includes taxes & fees
17 Aug - 18 Aug
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
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 SAR 676
SAR 1,865 total
includes taxes & fees
8 Sep - 9 Sep
Comfortable Berkshires retreat on mtn resort, SISO
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 SAR 713
SAR 1,656 total
includes taxes & fees
17 Aug - 18 Aug
Near Tanglewood: Historic Summer Retreat
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."
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is SAR 889
SAR 1,886 total
includes taxes & fees
3 Sep - 4 Sep
Cheerful 3-bedroom cottage with woodstove
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. "
Perfect House In Hillsdale, Brings Friends & Fam
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 SAR 1,407
SAR 1,941 total
includes taxes & fees
28 Aug - 29 Aug
Bungalow in the Berkshires
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, (1)
"Absolutely AMAZING house beautiful inside and out the features are absolutely amazing!! Carl the host is super nice. Definitely 100% recommend staying here! "
The price is SAR 822
SAR 1,833 total
includes taxes & fees
10 Sep - 11 Sep
NEW RENO Historic Creamery in Berkshires w/hot tub
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."
Historic Berkshires Home Near Tanglewood, Trails & Wineries
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

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

3-bedroom house in beautiful Berkshires, close to amenities!
Great Barrington Get Away
Fridge, microwave, oven, stovetop

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 SAR 1,220
SAR 2,096 total
includes taxes & fees
14 Sep - 15 Sep
Great Barrington Get Away
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Exterior

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

9.8 out of 10, Exceptional, (71)
"We had a wonderful stay, thank you! "
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 SAR 1,595
SAR 2,993 total
includes taxes & fees
28 Aug - 29 Aug
Spacious 5-bedroom house in charming Lee with WiFi
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 SAR 778
SAR 1,117 total
includes taxes & fees
14 Sep - 15 Sep
Experience Timeless Elegance in The Edith Wharton Room!
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 SAR 2,057
SAR 3,926 total
includes taxes & fees
20 Aug - 21 Aug
Hancock Village Inn at Jiminy Peak
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great value for families! The welcoming staff, location (Lenox/Pittsfield border), spacious suite, and ample amenities made for a fantastic vacation. No free breakfast but there are several dining options and markets nearby. Gorgeous view of the sunset from the upper floors. There was a note of upcoming renovations so looking forward to what else they have in store. "
Anonymous traveler 2-night trip
Posted 15 hours ago
Berkshire Mountain Lodge