Search for Cheap Deals on
Hotels in Chatham

Choose from 1590 Chatham Hotel Deals

Comfort Inn & Suites East Greenbush - Albany
Comfort Inn & Suites East Greenbush - Albany
2.5 out of 5
99 Miller Rd, Castleton-on-Hudson, NY
  • 37 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Castleton-on-Hudson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
8.4/10 Very Good! (959 reviews)
Home Away From Hone
"We travelled from Florida to Albany for a family funeral and Comfort Inn & Suites hotel accommodations were amazing. The queen double suite was very spacious and clean and the beds were super to sleep in. The complimentary breakfast had a great selection of favorite foods and the buffet was kept ..."

Reviewed on Jun 21, 2025

Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 34 min drive from The Mac-Haydn Theatre
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,830 reviews)
"second time stayed here. Love it!"

Reviewed on Jun 20, 2025

Vacation Village in the Berkshires
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 out of 5
12740 State Route 9 W, West Coxsackie, NY
  • 6 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in West Coxsackie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (890 reviews)
"The best hotel I never seen before. The employees are very kindless, very clean and the rooms are comfortable and super clean."

Reviewed on Jun 16, 2025

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
  • 28 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,002 reviews)
"It was clean and comfortable and a great location. Breakfast was good. Staff were helpful and pleasant."

Reviewed on Jun 22, 2025

Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 15 min drive from The Mac-Haydn Theatre
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on Jun 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
  • 12 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
"It was close to our entertainment for the night"

Reviewed on Jun 21, 2025

Best Western Plus Berkshire Hills Inn & Suites
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 8 min drive from The Mac-Haydn Theatre
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,003 reviews)
"Our experience was good, although The Yankee is nothing fancy, and there was a bug in the bathroom."

Reviewed on Jun 22, 2025

The Yankee, Trademark Collection by Wyndham
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 24 min walk from The Mac-Haydn Theatre
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.6/10 Excellent! (419 reviews)
"Great b&b, great Bfast, great location, easy parking!"

Reviewed on Jun 19, 2025

The Constance by the Lenox Collection
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 14 min drive from The Mac-Haydn Theatre
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,001 reviews)
"If you love history this place is for you!"

Reviewed on Jun 22, 2025

The Red Lion Inn
Prospect Berkshires
Prospect Berkshires
2 out of 5
50 Prospect Lake Rd, Egremont, MA
  • 28 min drive from The Mac-Haydn Theatre
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Catamount Aerial Adventure Park and Catamount ...
Prospect Berkshires
Berkshires Untold
Berkshires Untold
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 5 min drive from The Mac-Haydn Theatre
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (612 reviews)
"Nice upscale motel near Lenox. Rooms are well designed and furnished. But silly large “cages” around AC units block access to one of the beds from one side. The restaurant is not open on Monday. Nice full bar. Open fire-pit near the Lobby lounge. 5-8 minutes drive to many local dining options. Wi-fi ..."

Reviewed on Jun 24, 2025

Berkshires Untold
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
  • 15 min drive from The Mac-Haydn Theatre
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (796 reviews)
"All was great, except parking was quiet of walk"

Reviewed on Jun 13, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

Find cheap hotels in Chatham

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Chatham hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Chatham.

Choosing the right hotel in New York has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chatham’s 1,590 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as . In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chatham hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Chatham. No matter your reason for visiting Chatham, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Chatham hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Chatham for as low as .

How many hotels are there in Chatham?

With over 1,590 hotels in Chatham, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as .

How to find cheap car rentals in Chatham?

Finding a cheap car rental deal in Chatham is as easy as scoring cheap hotels in Chatham. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.