Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Find holiday rentals that suit your style
Aparthotels
Apartments
Our top choices for Cheshire holiday homes
1. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
Amit
The price is AU$741
includes taxes & fees
11 Nov - 12 Nov
2. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew 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. "
Joanna P.
The price is AU$291
includes taxes & fees
11 Nov - 12 Nov
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."
Stephen L.
The price is AU$677
includes taxes & fees
10 Nov - 11 Nov
4. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
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."
Jeri R.
The price is AU$288
includes taxes & fees
15 Nov - 16 Nov
5. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew 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)"
Leslie H.
The price is AU$314
includes taxes & fees
10 Nov - 11 Nov
6. Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Walk to Williams * Steam Sauna * Ritz-Carlton BedWilliamstown
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. "
Michelle B.
The price is AU$775
includes taxes & fees
24 Nov - 25 Nov
7. Hancock Village Inn Near Jiminy Peak
Hancock Village Inn Near Jiminy PeakHancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
Price F.
The price is AU$1,545
includes taxes & fees
18 Nov - 19 Nov
8. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth 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."
Diane
The price is AU$671
includes taxes & fees
10 Nov - 11 Nov
9. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
Robbie S.
The price is AU$798
includes taxes & fees
11 Nov - 12 Nov
10. Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to Williamstown
Bright Modern Secluded Vermont Home: Fish Pond + Trails, 5 Mins to WilliamstownPownal
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."
Claudette R.
The price is AU$849
includes taxes & fees
11 Nov - 12 Nov
11. Greylock Cabin
Greylock CabinFlorida
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!"
Margaret M.
The price is AU$659
includes taxes & fees
8 Dec - 9 Dec
12. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
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. "
Christine C.
The price is AU$588
includes taxes & fees
18 Nov - 19 Nov
13. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT RetreatBennington
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."
Malika R.
The price is AU$413
includes taxes & fees
11 Nov - 12 Nov
14. Private room with En-suite bathroom Marigold Room
Private room with En-suite bathroom Marigold RoomShelburne Falls
The price is AU$290
includes taxes & fees
12 Nov - 13 Nov
15. 5BR Berkshire Home Mins To The Mountain
5BR Berkshire Home Mins To The MountainCharlemont
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! "
Jason F.
The price is AU$1,408
includes taxes & fees
21 Nov - 22 Nov
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."
Brian C.
The price is AU$511
includes taxes & fees
10 Nov - 11 Nov
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."
Patricia O.
The price is AU$866
includes taxes & fees
10 Nov - 11 Nov
18. Shelburne Falls on Main
Shelburne Falls on MainShelburne 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."
maureen
The price is AU$568
includes taxes & fees
10 Nov - 11 Nov
19. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11
Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11Whitingham
10.0 out of 10, Exceptional, (16 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
Jonathan
The price is AU$694
includes taxes & fees
10 Nov - 11 Nov
20. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is AU$894
includes taxes & fees
11 Nov - 12 Nov
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.
Learn more about Cheshire
Get away to romantic Cheshire! Enjoy the skiing, hiking and natural setting.
Top reviews in Cheshire
Maple Terrace Motel
Maple Terrace MotelWilliamstown
10/10 Excellent
Just a wonderful motel - many special outdoor spaces to enjoy, including a fire pit and a pool. So pretty and beautifully maintained. The owner and his family welcomed us warmly and specially accommodated my husbands gluten free needs in a place where gluten free had been hard to find. Thank you for our wonderful stay.
Karen
