A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Cheshire vacation homes

Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
10.0 out of 10, Exceptional, (2 reviews)
"The room was clean and well appointed with ample bedding, towels, electrical outlets and fans (it was a very hot weekend). The house is spacious and the bathroom was well equipped. The host was very responsive to a question about off hours arrival. HIghly recommend."
United States
Mary M.
The price is AED 400
AED 501 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very Good, (10 reviews)
"The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay. "
United States
Russell R.
The price is AED 977
AED 2,452 total
includes taxes & fees
29 Jul - 30 Jul
Comfortable Berkshires retreat on mtn resort, SISO
Dining

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (4 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is AED 474
AED 819 total
includes taxes & fees
9 Aug - 10 Aug
Cozy Home in Pownal VT
Pool

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

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is AED 1,201
AED 2,326 total
includes taxes & fees
27 Jul - 28 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Outdoor dining

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
8.4 out of 10, Very Good, (9 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 1,154
AED 2,023 total
includes taxes & fees
26 Jul - 27 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Coffee/tea maker, fridge, microwave, stovetop

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (5 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is AED 646
AED 2,075 total
includes taxes & fees
27 Jul - 28 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Dining

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is AED 841
AED 1,781 total
includes taxes & fees
3 Aug - 4 Aug
A roomy remodeled retreat close to MassMoCA
Exterior

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Bennington
8.6 out of 10, Excellent, (35 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 507
AED 1,208 total
includes taxes & fees
22 Jul - 23 Jul
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveler
The price is AED 955
AED 1,603 total
includes taxes & fees
18 Aug - 19 Aug
The Greylock Cabin
Outdoor dining

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 2,117
AED 3,906 total
includes taxes & fees
22 Jul - 23 Jul
Hancock Village Inn Near Jiminy Peak
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is AED 479
AED 1,477 total
includes taxes & fees
22 Jul - 23 Jul
Two Brooks Lodge
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 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 871
AED 2,252 total
includes taxes & fees
22 Jul - 23 Jul
5BR Berkshire Home Mins To The Mountain
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (2 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is AED 750
AED 1,569 total
includes taxes & fees
28 Jul - 29 Jul
stylish Berkshires Retreat
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is AED 765
AED 1,720 total
includes taxes & fees
14 Aug - 15 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is AED 441
AED 792 total
includes taxes & fees
22 Jul - 23 Jul
Private bed with En-suite bathroom Marigold Room
Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 744
AED 1,639 total
includes taxes & fees
4 Aug - 5 Aug
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Iron/ironing board, WiFi, bed sheets

Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is AED 617
AED 1,374 total
includes taxes & fees
26 Jul - 27 Jul
Cozy private 2 bed apartment in Shelburne Falls
Fireplace, books, video library

Mountain Sanctuary Dome Rustic Solitude 5BR

Mountain Sanctuary Dome Rustic Solitude 5BR
Pownal
9.8 out of 10, Exceptional, (11 reviews)
"The facilities were as described; everything that was needed was easily accessible. When we couldn't find something, Nate was on hand to give us the guidance we needed."
United States
Cyndi L.
The price is AED 1,296
AED 2,348 total
includes taxes & fees
27 Jul - 28 Jul
Mountain Sanctuary Dome Rustic Solitude 5BR
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very Good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is AED 1,462
AED 2,642 total
includes taxes & fees
16 Aug - 17 Aug
Spacious Central Berkshires Home for Groups
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (83 reviews)
"Amazing property, close to town "
United States
Tricia E.
Enjoy comfortable elegance in this secluded grand home located in town
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"We only stayed one night. Breakfast was decent and room was clean."
James 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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