An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.

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Our top choices for Cheshire holiday homes

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
The price is £104
includes taxes & fees
18 Jun - 19 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

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)
"We had a great family getaway here! The hot tub was amazing and the views from the hot tub were perfect. What a beautiful location - quiet, peaceful and a fun space for kids to explore. We had an amazing time trekking out in the woods in the snow.Kitchen was well stocked and the treats, coffee and tea were a nice bonus. My kids enjoyed the extra games as well! Extremely quick responses from the host as well! Thanks for a good time, we are already thinking about coming back in the summer."
United States
Amanda H.
The price is £222
includes taxes & fees
17 Jun - 18 Jun
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 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 £154
includes taxes & fees
29 Jun - 30 Jun
Cozy Home in Pownal VT

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 £279
includes taxes & fees
17 Jun - 18 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"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 £334
includes taxes & fees
17 Jun - 18 Jun
stylish Berkshires Retreat

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is £381
includes taxes & fees
17 Jun - 18 Jun
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is £304
includes taxes & fees
15 Jul - 16 Jul
The Greylock Cabin

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 £284
includes taxes & fees
17 Jun - 18 Jun
Two Brooks Lodge

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is £290
includes taxes & fees
17 Jun - 18 Jun
Near Tanglewood: Historic Summer Retreat

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (25 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is £325
includes taxes & fees
30 Jun - 1 Jul
North Getaway Cottage

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, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is £419
includes taxes & fees
17 Jun - 18 Jun
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is £311
includes taxes & fees
17 Jun - 18 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

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 £361
includes taxes & fees
8 Jul - 9 Jul
Walk to Williams * Steam Sauna * Ritz-Carlton Bed

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
7.8 out of 10, Good, (7 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 £403
includes taxes & fees
19 Jun - 20 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is £588
includes taxes & fees
22 Jun - 23 Jun
Spacious 5-bedroom house in charming Lee with WiFi

Unique and Eclectic Small Town Suite Rental in Massachusetts

Unique and Eclectic Small Town Suite Rental in Massachusetts
Cummington
The price is £104
includes taxes & fees
19 Jun - 20 Jun
Unique and Eclectic Small Town Suite Rental in Massachusetts

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"It was a lovely four day stay. There was everything we needed in the large kitchen. The livingroom was comfortable and spacious. We especially enjoyed the back deck and the view of the mountains. If we return to the area, we'll definitely stay here again."
United States
Marianne B.
The price is £349
includes taxes & fees
17 Jul - 18 Jul
Riverbend Berkshire East Basecamp - 3 bedrooms available

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (20 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is £859
includes taxes & fees
24 Jun - 25 Jun
Hancock Village Inn Near Jiminy Peak

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is £356
includes taxes & fees
7 Jul - 8 Jul
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"Kind and responsive host."
United States
Javier
The price is £399
includes taxes & fees
18 Jun - 19 Jun
Comfortable Berkshires retreat on mtn resort, SISO
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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