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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Cheshire vacation homes

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 ￥22,791
￥58,809 total
includes taxes & fees
May 10 - May 11
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
TV

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ￥32,007
￥56,982 total
includes taxes & fees
May 10 - May 11
Florida Mountain Log Cabin
Smart TV

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 ￥18,149
￥31,882 total
includes taxes & fees
May 10 - May 11
Cozy Home in Pownal VT
Exterior

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 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 ￥31,655
￥69,932 total
includes taxes & fees
May 11 - May 12
North Getaway Cottage
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 ￥37,048
￥95,860 total
includes taxes & fees
May 10 - May 11
5BR Berkshire Home Mins To The Mountain
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ￥56,119
￥112,622 total
includes taxes & fees
May 10 - May 11
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
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, (9 reviews)
"Kind and responsive host."
United States
Javier
The price is ￥25,168
￥84,452 total
includes taxes & fees
May 9 - May 10
Comfortable Berkshires retreat on mtn resort, SISO
Exterior

The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (6 reviews)
"the hosts were great very helpful and pleasant"
United States
Ron L.
The price is ￥37,068
￥63,700 total
includes taxes & fees
Jun 7 - Jun 8
The Greylock Cabin
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
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 ￥42,066
￥77,371 total
includes taxes & fees
May 9 - May 10
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
TV

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 ￥44,528
￥78,750 total
includes taxes & fees
May 13 - May 14
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.4 out of 10, Exceptional, (3 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is ￥27,356
￥86,675 total
includes taxes & fees
May 9 - May 10
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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 ￥18,606
￥60,923 total
includes taxes & fees
May 10 - May 11
Two Brooks Lodge
Property grounds

Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (3 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ￥32,554
￥73,186 total
includes taxes & fees
May 22 - May 23
Riverbend Berkshire East Basecamp - 3 bedrooms available
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Breakfast was ok. It was difficult to adjust room temp. Very inconvenient to take luggage to second floor for seniors. There should be a lif."
RAI AJIT 2-night trip
Posted 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Cheshire

Cheshire Vacation Homes information

Number of reviews
121
Accommodation
281 Vacation Homes
Lowest Price
￥31,882
Highest Price
￥179,608