Vacation Homes in Cheshire
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Featured Vacation Homes in Cheshire

Peace and quiet on the lake

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown

19th c. Barn in the Berkshires

Charming Berkshire Retreat-Minutes to Williamstown

3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome

120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views

Contemporary Berkshire Home with Views of Taconic Golf Course

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Top trending hotels in Cheshire

Hampton Inn & Suites Berkshires-Lenox
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 | 282 Vacation Homes |
|---|---|
Lowest Price | CA $148 |
Highest Price | CA $302 |
Popular accommodation | Peace and quiet on the lake, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Mid Century Modern 4 bedroom home with sweeping mountain views in Williamstown, 19th c. Barn in the Berkshires, Charming Berkshire Retreat-Minutes to Williamstown, 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome, 120-Acre Private Estate: Heated Pool, Fire Pit, Apple Orchard, Catskills Views, Contemporary Berkshire Home with Views of Taconic Golf Course, Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village., Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay, Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included, Secluded Family Getaway w/ On-Site Creek in Hawley |






