Cheshire Vacation Rentals
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Vacation Rentals in Cheshire
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay
East Chatham NY
Located in East Chatham, this vacation home is in the mountains, within a 15-minute drive of Queechy Lake and The Mac-Haydn Theatre.
Hot Tub
Kitchen
Peace and quiet on the lake
Becket MA
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Pittsfield MA
Located in Pittsfield, this vacation home is on a lake, within a 5-minute drive of Pittsfield Dog Park and Crane Museum of Papermaking.
Hot Tub
Kitchen
Contemporary Berkshire Home with Views of Taconic Golf Course
Williamstown MA
Located in Williamstown, this vacation home is within a 5-minute drive of Williams College Taconic Golf Course and Williams College.
Kitchen
Washer
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Lenox MA
With a stay at this vacation home, you'll be centrally located in Lenox, within a 10-minute drive of Tanglewood Music Center and National Shrine of the Divine Mercy.
Pool
Hot Tub
Secluded Family Getaway w/ On-Site Creek in Hawley
Hawley MA
Located in Charlemont, this vacation home is on the waterfront, within a 15-minute drive of Zoar Outdoor/Deerfield Valley Canopy Tours and Berkshire East Ski Resort.
Kitchen
Washer
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Lanesborough MA
Located in Lanesborough, this vacation home is on a lake, within a 10-minute drive of St Mary's of the Assumption Church and Crane Museum of Papermaking.
Hot Tub
Kitchen
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough MA
With a stay at this vacation home in Lanesborough, you'll be within a 10-minute drive of Crane Museum of Papermaking and Barrington Stage Company.
Hot Tub
Kitchen
Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay
Lee MA
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of National Shrine of the Divine Mercy and Tanglewood Music Center.
Kitchen
Washer
Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown
Williamstown MA
Located in Williamstown, this vacation home is a 2-minute drive from Green Mountain National Forest and 7 minutes from Farm Museum.
Washer
Dryer
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 Vacation Rentals essential information
Accommodation | 281 Vacation Rentals |
|---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, Peace and quiet on the lake, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Contemporary Berkshire Home with Views of Taconic Golf Course, Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++, Secluded Family Getaway w/ On-Site Creek in Hawley, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay, Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown, Charming 2-bedroom house in peaceful Lee, Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included |