*Savings based on Hot Rate® hotel bookings made in the previous 12 months as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.
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Chatham is calling — find the perfect hotel
Everyone wants to score a deal on travel, but price is just one factor to consider when booking an unforgettable hotel. Whether you’re visiting family, attending a conference or taking a well-earned vacation in Chatham, having an awesome experience should be a no-brainer.
Hotwire will hook you up! From restful nights near your flight to that prime spot in the city’s heart, we’ve done our research to bring the best options to your fingertips. Book your Chatham hotel with us now and start your next adventure.
You’re not the average traveler — and we know it
You’ve done your homework and know exactly where you want to go. We’re here to help with some Hotwire travel geek-approved tips on how to save on your booking.
Get away for the weekend
Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.
Give yourself some wiggle room
If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.
Plan around big events
Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.
Noodle over new adventures
Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.
Top Booked Hotels in Chatham
- Vacation Village in the Berkshires
- Holiday Inn & Suites Pittsfield-Berkshires
- The Red Lion Inn
- Best Western Plus Berkshire Hills Inn & Suites
- Hampton Inn & Suites Berkshires Lenox
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- Hilton Garden Inn Lenox Pittsfield
- Jiminy Peak Mountain Resort
- Holiday Inn Club Vacations Oak n' Spruce Resort
- The Black Swan Inn, Ascend Hotel Collection
- Courtyard by Marriott Lenox Berkshires
- Yankee Inn
More to Explore
- Hotels near The Mac-Haydn Theatre
- Hotels near Jiminy Peak Mountain Resort
- Hotels near Ski Butternut
- Hotels near Tanglewood Music Center
- Hotels near Norman Rockwell Museum
- Hotels near Lee Prime Outlets
- Hotels near Catamount Ski Area
- Hotels near National Shrine of the Divine Mercy
- Hotels near Cranwell Golf Club
- Hotels near Bousquet Ski Area
- Hotels near Destroyer Escort Historical Museum
- Hotels near Hancock Shaker Village
- Hotels near Van Alen House
- Hotels near October Mountain State Forest
- Hotels near Pittsfield State Forest
- Hotels near USS Slater
- Hotels near Taconic Trail State Park
- Hotels near Olana State Historic Site
- Hotels near Shakespeare and Company
- Hotels near Hudson Opera House
- Hotels near The Mount
- Hotels near Beartown State Forest
- Hotels near Hudson Area Library
- Hotels near Lake Taghkanic State Park
- Hotels near New Lebanon Library
- Hotels near Lee Library
- Hotels near Claverack Library
- Hotels near Goose Pond Reservation
- Hotels near The Bookstore
- Hotels near Shaker Museum and Library
- Hotels near Catamount Aerial Adventure Park
- Hotels near Lenox Library
- Hotels near Colonial Theater
- Hotels near Kennedy Park
- Hotels near Dutchman’s Landing
- Hotels near Zema's Nursery
- Hotels near Housatonic River Walk
- Hotels near Brookview Station Winery
- Hotels near Kinderhook Cemetery
- Hotels near Berkshire Museum
- Hotels near Naumkeag
- Hotels near Greene County Council on the Arts
- Hotels near Berkshire Botanical Garden
- Hotels near Schantz Galleries
- Hotels near Martin Van Buren National Historic Site
- Hotels near FASNY Museum of Firefighting
- Hotels near Max and Lillian Katzman Theater
- Hotels near Valatie Free Library
- Hotels near Furnace Brook Winery at Hilltop Orchards
- Hotels near Bidwell House Museum
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