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Compare 51 Cottages in Cheshire with updated reviews, rates, and availability.
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
Cozy Cottage in the Woods
Cozy Cottage in the Woods
10.0 out of 10, Exceptional, (1)
Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (11)
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Cozy Berkshire cottage with fireplace.
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
Morgan House on Crooked Lake
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
Beachwood Cottage
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
Caretaker's Cottage: 20 minutes to Tanglewood
Caretaker's Cottage: 20 minutes to Tanglewood
10.0 out of 10, Exceptional, (3)
Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
Cottage in the Clouds With Mountain Views
Cottage in the Clouds With Mountain Views
10.0 out of 10, Exceptional, (1)
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
10.0 out of 10, Exceptional, (1)
Picturesque Cottage with Sunroom on Ashmere Lake!
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
Berkshires - Charming Lakefront Cottage
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Private Lake Cottage on 3 acres w/350 sq. ft. deck
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
Peaceful Family Home w/ Fire Pit & Large Yard
Peaceful Family Home w/ Fire Pit & Large Yard
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Peaceful Seasonal lake front cottage with view of Burden Lake
Peaceful Seasonal lake front cottage with view of Burden Lake
10.0 out of 10, Exceptional, (2)
Black Bear Mountain Cottage
Black Bear Mountain Cottage
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.
Other property types in Cheshire
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (857)
The price is $154
$169 total
includes taxes & fees
May 30 - May 31
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
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.
Cheshire Cottages information
Number of reviews | 142 |
---|---|
Accommodation | 51 Cottages |
Lowest Price | |
Highest Price |
Frequently asked questions
Recent reviews of Cheshire hotelsExpedia verified reviews
5/5 Excellent
"My husband and I had a lovely stay at the Black Swan Inn. The hotel was very comfortable, the breakfast was great, and the dinner at the Indian restaurant was delicious! Being right on the lake made for a very relaxing time reading in the Adirondack chairs. We also very much enjoyed kayaking around the lake. We will be back!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 1 day ago
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