A lake surrounded by autumn-colored trees and hills.

Search Vacation Homes in Cheshire

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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 1,183
AED 2,543 total
includes taxes & fees
23 Nov - 24 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 723 total
includes taxes & fees
10 Nov - 11 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.
The price is AED 988
AED 1,732 total
includes taxes & fees
19 Nov - 20 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

4. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (15 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.
The price is AED 426
AED 716 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Home in Pownal VT

5. 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 782 total
includes taxes & fees
10 Nov - 11 Nov
1800s Carriage house in Berkshires / Hudson Valley

6. 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
24 Nov - 25 Nov
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

7. 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

8. 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
A roomy remodeled retreat close to MassMoCA

9. 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 2,039 total
includes taxes & fees
9 Dec - 10 Dec
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

10. 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.
The price is AED 1,157
AED 2,160 total
includes taxes & fees
11 Nov - 12 Nov
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown

11. 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.
The price is AED 1,121
AED 1,658 total
includes taxes & fees
10 Dec - 11 Dec
Greylock Cabin

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 602
AED 1,493 total
includes taxes & fees
10 Nov - 11 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley

13. 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.
The price is AED 422
AED 1,055 total
includes taxes & fees
11 Nov - 12 Nov
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

14. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
Private room with En-suite bathroom Marigold Room

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.
The price is AED 2,070
AED 3,617 total
includes taxes & fees
21 Nov - 22 Nov
5BR Berkshire Home Mins To The Mountain

16. 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)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is AED 536
AED 1,312 total
includes taxes & fees
10 Nov - 11 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

17. 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 2,218 total
includes taxes & fees
10 Nov - 11 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!

18. Shelburne Falls on Main

Shelburne Falls on Main
Shelburne Falls
10.0 out of 10, Exceptional, (1 review)
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
Shelburne Falls on Main

19. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Very peaceful backyard!! Great back deck!!"
United States
Jacqueline M.
The price is AED 1,315
AED 2,489 total
includes taxes & fees
10 Dec - 11 Dec
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

20. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is AED 1,253
AED 2,257 total
includes taxes & fees
10 Nov - 11 Nov
Secluded Family Home in Serene Stockbridge Woods
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire Hotel Reviews