Compare Cheshire Resorts

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 Resorts 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

    Harbour House Inn

    Harbour House Inn

    725 North State Road, Cheshire, MA
    $262 nightly
    The price is $277 total per night from Oct 14 to Oct 15
    $277 total
    Oct 14 - Oct 15
    Total with taxes and fees
    9.6/10 Exceptional! (38 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $112 nightly
    The price is $125 total per night from Oct 30 to Oct 31
    $125 total
    Oct 30 - Oct 31
    Total with taxes and fees
    8.6/10 Excellent! (2,039 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (678 reviews)

Resort Hotels

Resort hotels in Cheshire
Find your next great getaway when you book at a resort hotel in Cheshire. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Cheshire at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Cheshire is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Cheshire
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Cheshire resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Cheshire Resorts essential information

Accommodation
34 Resorts
Lowest Price
$125
Highest Price
$277
Popular accommodation
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx., Bentley Brook the perfect home base for exploring nearby Berkshire County, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Bentley Brook the perfect home base for exploring nearby Berkshire County, COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY., Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!, Bentley Brook the perfect home base for exploring nearby Berkshire County, 1 Bd - Vacation Village in the Berkshires, Bentley Brook - Hancock, MA - 2BD, Sleeps 8ppl - A