Compare Cheshire Villas

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Cheshire

Don't see what you're looking for?
See all available properties in Cheshire
View all properties
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.

Hotel Options in Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $126 nightly
    The price is $141 total per night from Jan 4 to Jan 5
    $141 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.6/10 Excellent! (2,182 reviews)
    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $124 nightly
    The price is $138 total per night from Jan 27 to Jan 28
    $138 total
    Jan 27 - Jan 28, 2026
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    The Williams Inn

    The Williams Inn

    101 Spring Street Williamstown MA
    $181 nightly
    The price is $203 total per night from Jan 8 to Jan 9
    $203 total
    Jan 8 - Jan 9, 2026
    Total with taxes and fees
    9.6/10 Exceptional! (554 reviews)

Luxury Villas

Book luxury villas in Cheshire
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Cheshire. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Cheshire, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Cheshire
You won’t have a problem finding your own space in Cheshire. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Cheshire on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Cheshire rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Cheshire Villas essential information

Accommodation
2 Villas
Lowest Price
$138
Highest Price
$936
Popular accommodation
The Kemble- Built by a US Secretary of State in Lenox, Vermont Vacation Villa—Grapevine Getaway