Vacation Homes in Cheshire
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Vacation Homes in Cheshire
![Private Lake House in the Berkshires](https://images.trvl-media.com/lodging/75000000/74800000/74798400/74798362/e9d66013_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Private Lake House in the Berkshires
![Hearts Desire is a furnished whole house in a small, colorful garden center.](https://images.trvl-media.com/lodging/70000000/69770000/69763300/69763258/128e06d4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hearts Desire is a furnished whole house in a small, colorful garden center.
![Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!](https://images.trvl-media.com/lodging/92000000/91120000/91112800/91112738/47b8e5f1_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
![Hawley Home w/ Deck: 4 Mi to Berkshire East Resort](https://images.trvl-media.com/lodging/102000000/101310000/101300500/101300497/90deece8_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
![Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort](https://images.trvl-media.com/lodging/34000000/33100000/33090400/33090325/0e014173_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
![Tranquil 3-BR Waterfront Retreat](https://images.trvl-media.com/lodging/91000000/90920000/90910900/90910813/ee441255_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Tranquil 3-BR Waterfront Retreat
![Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/864e23b6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
![Cozy Home In The Berkshires, Pet Friendly with fenced in yard!](https://images.trvl-media.com/lodging/33000000/32630000/32627100/32627001/d586cd2f_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
![Private Cabin On Over 12 Acres Of Woods!](https://images.trvl-media.com/lodging/96000000/95060000/95059800/95059773/22500982_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Private Cabin On Over 12 Acres Of Woods!
![Private Suite with a Sweet View. Spacious, close to town, dog friendly](https://images.trvl-media.com/lodging/35000000/34870000/34869800/34869766/ae48a61e_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Private Suite with a Sweet View. Spacious, close to town, dog friendly
![1810 Brook Side Mill/House / EV Level 2 Charging on Site](https://images.trvl-media.com/lodging/55000000/54180000/54172400/54172390/f4cdf3e6_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Top trending hotels in Cheshire
![Life House Berkshires](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
Life House Berkshires
Vacation Rentals in Cheshire
What kind of vacation do you want in Cheshire? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Cheshire that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Cheshire, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Cheshire Vacation Homes essential information
Accommodation | 230 Vacation Homes |
---|---|
Lowest Price | CA $163 |
Highest Price | CA $1,106 |
Popular accommodation | Private Lake House in the Berkshires , Hearts Desire is a furnished whole house in a small, colorful garden center., Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!, Hawley Home w/ Deck: 4 Mi to Berkshire East Resort, Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort, Tranquil 3-BR Waterfront Retreat, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Cozy Home In The Berkshires, Pet Friendly with fenced in yard!, Private Cabin On Over 12 Acres Of Woods!, Private Suite with a Sweet View. Spacious, close to town, dog friendly, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Historic New Lebanon Hideaway on 33 Private Acres! |