Cheshire Holiday Homes

Check availability on Holiday Homes in Cheshire

4 Nov - 5 Nov

Tonight

5 Nov - 6 Nov

Tomorrow night

Featured Holiday Homes in Cheshire

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Whitingham, VT

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During your stay at this holiday home, you'll be close to Readsboro Community Library. Features include laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Sijainti!!! Sijainti!!! Berkshire Glamour (ja mukavuus) kohtaa kaupungin ja maan

Stockbridge, MA

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During your stay at this holiday home, you're just a quick walk from Stockbridge Bowl. Laundry facilities are available. The holiday home includes amenities such as free WiFi and a kitchen.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox, MA

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During your stay at this holiday home, you'll be within walking distance of Wyndhurst Golf & Club. Enjoy features like an outdoor pool and laundry facilities. The holiday home offers a private pool and in-room jetted baths.

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee, MA

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During your stay at this holiday home, you're just a quick walk from Greenock Country Club. You'll find features such as laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape

West Stockbridge, MA

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During your stay at this holiday home, you'll be close to Richmond Free Public Library. The holiday home offers free WiFi and a kitchen.

Spacious 5-bedroom house in charming Lee with WiFi

Lee, MA

€704

1 Dec - 2 Dec

includes taxes & fees

During your stay at this holiday home, you're just a quick walk from Housatonic River. You'll find features such as laundry facilities and an arcade/games room. The holiday home includes amenities such as a kitchen and 3.5 bathrooms.

Rauha ja hiljainen järvellä

Becket, MA

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Our customers tell us they can't get enough of this holiday home's great location. During your stay, you'll be close to Pyramid Lake. Laundry facilities are available. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Contemporary Berkshire Home with Views of Taconic Golf Course

Williamstown, MA

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During your stay at this holiday home, you'll be within walking distance of Williams College Taconic Golf Course. You'll find features such as laundry facilities. Enjoy your stay with amenities like in-room jetted baths and a kitchen in the holiday home.

Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.

Lee, MA

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During your stay at this holiday home, you'll be within walking distance of Berkshire Mountain Country Store. Features include laundry facilities. Free WiFi and in-room jetted baths are available in the holiday home.

Hearts Desire is a furnished whole house in a small, colorful garden center.

Lanesborough, MA

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During your stay at this holiday home, you'll be close to Jiminy Peak Mountain Resort. You'll find features such as 1 hot tub and laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Bright Modern Secluded Vermont Home: Trout Pond + Trails, 5 Mins to Williamstown

Pownal, VT

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During your stay at this holiday home, you're just a quick walk from Green Mountain National Forest. Features include laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Secluded 4 bedroom home with sweeping mountain views in Williamstown

Williamstown, MA

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During your stay at this holiday home, you'll be within walking distance of Green Mountain National Forest. Enjoy your stay with amenities like 2 bathrooms and a TV in the holiday home.

Kenraali Williams Estate House Lenox / Stockbridge

Stockbridge, MA

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During your stay at this holiday home, you'll be within walking distance of Berkshire Theatre Festival. Laundry facilities and an arcade/games room are available. The holiday home includes amenities such as a private pool and a kitchen.

Woodland 5-BR Retreat 5-Min to Jiminy Peak

Hancock, MA

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During your stay at this holiday home, you'll be close to Jiminy Peak Mountain Resort. Features include laundry facilities. A private pool and a kitchen are available in the holiday home.

StrautmanHaus - All-Season Chalet at Berkshire East

Charlemont, MA

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During your stay at this holiday home, you're just a quick walk from Berkshire East Ski Resort. Laundry facilities are available. A kitchen and 2 bathrooms are available in the holiday home.

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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.