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Compare 288 Vacation Homes in Cheshire with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (246)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
Berkshire Village Carriage House - Super Private!!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
19 May - 20 May
Hancock Village Inn at Jiminy Peak

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (73)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "
Peace and quiet on the lake

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (72)
"Going to the Berkshires this is a great place to stay. It is within walking distance to over 8 restaurants in downtown Lenox. Great gas stove and comfortable bed. Owner makes sure your stay is great. Would stay here again. "
Heart of Lenox Walk to Town Cozy Cottage!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (5)
"Our group of 8 were happy in this comfy home. The kitchen was well appointed with everything we needed. The bedding, towels and toiletries provided were very much appreciated. The cozy living room with the pellet stove has a beautiful view for morning coffee. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"The location is absolutely beautiful, the pool was great, and there was plenty of room for everyone. This was our second time staying at this house and we will be back."
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Absolutely no complaints. Great place to stay, great host! Happy 2025 wishes from our family to everyone reading this post! "
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (42)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Lakeside 5-BR Home in Idyllic Berkshires

10.0 out of 10, Exceptional, (2)
"Celebrated a birthday with a group of old friends. Great location near Lee. Enjoyed the lake views. Fires inside and outside. Home is well decorated and clean."
Lakeside 5-BR Home in Idyllic Berkshires

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AED 775
AED 1,905 total
includes taxes & fees
4 Jun - 5 Jun
2.5mi from the lake! Fire pit, arcade, yard games!

Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

10.0 out of 10, Exceptional, (34)
"We had a wonderful time at this property! It was perfect for what we wanted- a place to ourselves in nature with beautiful views. Host was great! Would definitely recommend! "
Family-Friendly Home With Incredible Berkshire Views And A Private Swim Pond

Stockbridge Village Cottage With Mountain View’s and walk to town

10.0 out of 10, Exceptional, (58)
"Great house, fully stocked kitchen, lots of cozy places to snuggle up, great location"
Stockbridge Village Cottage With Mountain View’s and walk to town

Sophisticated Lenox Retreat by Evergreen Home

9.8 out of 10, Exceptional, (9)
"Very quaint location, clean property, and great place to stay"
Sophisticated Lenox Retreat by Evergreen Home

Country Living just minutes from Everything!

10.0 out of 10, Exceptional, (28)
"Very nice, very clean property. Everything you need. Communication with owner is excellent. My family and I were extremely comfortable here!"
Country Living just minutes from Everything!
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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Other property types in Cheshire

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1805)
"The property was clean and the staff very accommodated."
The price is AED 403
AED 490 total
includes taxes & fees
18 May - 19 May
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 493
AED 550 total
includes taxes & fees
18 May - 19 May
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
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.