We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
WINNER WONDERLAND
Win Big When You Book on TripAdvisor

Hotels Near Cheshire, Massachusetts

View map
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Sponsored by:
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Check In Check Out
    Show Prices
    Sort by:
    Distance
    Ranking
    Lowest Price
    Distance
    Clear all
    Your Selections
      Free Wifi Budget City Center Luxury Free Breakfast Mid-range Pool Free Parking Family-friendly Quiet Restaurant Pets Allowed Suites Kitchenette Bar/Lounge Fitness center Room Service Business Classic & up Internet & up Independent Hotels Air Conditioning Business Center & up Meeting Rooms Non-Smoking Hotel Concierge Accessible rooms $ $$ $$$ $$$$ Ski-In / Ski-Out Resort Club Wyndham Charming EconoLodge Boutique Trendy Romantic Crowne Plaza Green Within 5 mi Within 10 mi Within 25 mi
    Price per night
    Enter dates & see best prices
    to
    Traveler Rating
    Location
    Any Distance
    from
    Amenities
    More
    Amenities
    Accommodation
    Hotel class
    Style
    More
    Style
    Hotel brand
    Show more filters Show fewer filters
    TripAdvisor members only.
    Login for exclusive access to hotel deals up to 40% off
    Login to get best prices
    We're sorry, Cheshire doesn't have any hotels.
    Sponsored
    6.1 miles from Cheshire
    Wyndham at Bentley Brook
    $$$$
    Show Prices
    4.8 miles from Cheshire
    Weathervane Motel
    $$$$
    Show Prices
    5.0 miles from Cheshire
    The Springs Inn
    $$$$
    Show Prices
    5.8 miles from Cheshire
    Bascom Lodge
    $$$$
    Show Prices
    6.0 miles from Cheshire
    Econo Lodge
    $$$$$$
    Show Prices
    Wyndham at Bentley Brook
    $$$$
    Show Prices
    Vacation Village in the Berkshires
    $$$$
    Show Prices
    Country Inn at Jiminy Peak
    $$$$
    Show Prices
    Berkshire Valley Inn
    $$$$$$$$
    Show Prices
    8.0 miles from Cheshire
    Hotel on North
    $$$$$$$$
    Show Prices
    Crowne Plaza Pittsfield
    $$$$$$$
    Show Prices
    Yankee Suites Extended Stay
    $$$$$$$$
    Show Prices
    8.8 miles from Cheshire
    Berkshire Inn
    $$$$$
    Show Prices
    Berkshire Hills Country Inn
    $$$$$$$
    Show Prices
    *Prices above are provided by partners for one room, double occupancy and do not include all taxes and fees. Please see our partners for full details. Any taxes and fees displayed, if applicable, are estimates only. Please see further details from our partners, who set the prices. Before you complete any reservation, we recommend that you verify the total cost including taxes and fees.