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Our top choices for Cheshire vacation homes

1. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AED 591
AED 1,886 total
includes taxes & fees
5 Nov - 6 Nov
Comfortable Berkshires retreat on mtn resort, SISO

2. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is AED 257
AED 719 total
includes taxes & fees
5 Nov - 6 Nov
NEW RENO - Chalet-style farm loft near Tanglewood

3. 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
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is AED 312
AED 778 total
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley

5. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (13 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
United States
Jeri R.
Cozy Home in Pownal VT

6. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 908
AED 1,691 total
includes taxes & fees
4 Dec - 5 Dec
A roomy remodeled retreat close to MassMoCA

7. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is AED 992
AED 1,995 total
includes taxes & fees
22 Nov - 23 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is AED 746
AED 2,087 total
includes taxes & fees
5 Nov - 6 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

9. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,310
AED 4,007 total
includes taxes & fees
17 Nov - 18 Nov
Hancock Village Inn Near Jiminy Peak

10. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
Greylock Cabin

11. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Pownal
10.0 out of 10, Exceptional, (41 reviews)
"We enjoyed our stay! The home was clean, well-stocked, and very comfortable. I loved the serenity of the location. We took walks on trails through the forest and enjoyed the peace and quiet."
United States
Claudette R.
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is AED 657
AED 1,560 total
includes taxes & fees
9 Nov - 10 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley

13. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 422
AED 726 total
includes taxes & fees
8 Nov - 9 Nov
Private room with En-suite bathroom Marigold Room

14. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

15. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
5BR Berkshire Home Mins To The Mountain

16. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
United States
Delaney M.
The price is AED 1,157
AED 2,393 total
includes taxes & fees
8 Nov - 9 Nov
Ellie’s Overlook, best view in the Berkshires!

17. 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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 536
AED 1,312 total
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

18. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
The price is AED 3,328
AED 4,639 total
includes taxes & fees
5 Nov - 6 Nov
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

19. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is AED 1,167
AED 2,206 total
includes taxes & fees
5 Nov - 6 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!

20. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
United States
neil s.
The price is AED 1,074
AED 2,086 total
includes taxes & fees
5 Nov - 6 Nov
Spacious Central Berkshires Home for Groups
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 Cheshire Hotel Reviews