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Top hotels

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
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate ...
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

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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"Nice place to stay. Good breakfast."

Reviewed on Jun 23, 2025

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The Yankee, Trademark Collection by Wyndham
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi ...
"I had excellent stay at the Red Lion Inn"

Reviewed on Jun 16, 2025

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The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks ...
"We always stay here because it’s the best value and so beautiful."

Reviewed on Jun 23, 2025

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Vacation Village in the Berkshires
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
A gym, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public ...
"very polite attentive check in."

Reviewed on Jun 18, 2025

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The Constance by the Lenox Collection
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

2.5 out of 5
99 Miller Rd, Castleton-on-Hudson, NY
Fully refundableReserve now, pay when you stay
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet ...
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

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Comfort Inn & Suites East Greenbush - Albany
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
Fully refundable
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour ...
"Very new and clean. Nice decor and delish breakfast !"

Reviewed on Jun 15, 2025

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Holiday Inn Express Hotel & Suites West Coxsackie 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
Fully refundableReserve now, pay when you stay
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the ...
"It was close to our entertainment for the night"

Reviewed on Jun 21, 2025

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Best Western Plus Berkshire Hills Inn & Suites
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. ...
"Clean, quiet hotel in Great Barrington. Staff members were kind and attentive. Easy parking and check in / check out."

Reviewed on Jun 17, 2025

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Quality Inn
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See all available properties in Chatham
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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.

Chatham Hotel & Travel Guide\n

There isn't a big range of places to stay within easy driving distance of Chatham's center. Be sure to book well in advance if you'd like to stay close to Chatham's action.

The Inn At Richmond, Massachusetts, which is the nearest hotel, is 11 miles (18 kilometers) from the heart of downtown Chatham. A second handy Travelocity-listed option is the Wyndham Bentley Brook, which is situated in Massachusetts, 20 miles (33 kilometers) from the center of Chatham.

The Stockbridge Country Inn is 12 miles (19 kilometers) from the center of Chatham. Also, the Fairfield Inn and Suites by Marriott Lenox Great Barrington is situated 14 miles (23 kilometers) away. You might like to check in to the Holiday Inn Express Hotel & Suites Great Barrington or the Jiminy Peak Mountain Resort.

After you've thoroughly explored Chatham, why don't you discover a little more of the region? The Hudson Valley vicinity boasts plenty of things to check out. Explore Hudson Valley's historic bridges and don't forget to fall in love with the area's rivers. Enlightened travelers in this corner of United States of America enjoy rock climbing and hiking.

On the hunt for things to do? You could spend a few hours seeing Marist College and Culinary Institute of America, which can be found in Poughkeepsie, 50 miles (77 kilometers) southwest of Chatham. When you visit Poughkeepsie, be sure to check out the Buttermilk Falls Inn and Residence Inn by Marriott Poughkeepsie. 35 miles (58 kilometers) southwest of Chatham, you will reach Kingston, home to the Best Western Plus Kingston Hotel And Conference Center and Hampton Inn Kingston. The El Paso Winery and Old Dutch Church are popular places to experience when in Kingston.

Prior to departing from Hudson Valley, you sure ensure you enjoy enthusiastic locals watching an exciting game of sport. Make your way to Times Union Center, located to the northwest of Chatham. For tourists who like the thought of staying close to the game, book a room in the Hilton Albany or TownePlace Suites by Marriott Albany Downtown/Medical Center.

When you are traveling through Albany International Airport and hope to book a room in the area, have a look at Albany Marriott or Homewood Suites by Hilton Albany.

Frequently asked questions

What are the top kid-friendly hotels in Chatham?
Family getaways are where wonderful memories are made, but traveling with young ones can be demanding. These kid-friendly Chatham hotels offer perks that aim to keep young and old alike relaxed and happy: You'll be well looked after at The Honeydew: Cozy*hot tub*fire pit*walk to dinner. It comes with a firepit, a fireplace and a knack for making families feel at home. Alternatively, spend your nights in Chatham at Charming Farm House on 460 Acre Working Farm. Take advantage of a deck, animal viewing activities and more here.
Where can I find cheap hotels in Chatham?
At Travelocity you'll find really nice hotels in Chatham at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Chatham rather than in Chatham. We may find you even better rates, too.
How do I find the best Chatham hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Chatham then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Chatham?
The cheapest hotel in Chatham is . This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Chatham?
There are 1,589 hotels in Chatham on Travelocity.
What are the best hotels in Chatham?
Chatham has so many great hotels to choose from at Travelocity --- and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Chatham for you!
When is the best time to visit Chatham?
If you want the joy of a fun-filled trip in peak season, visit Chatham during February, March and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as June, September and October.
When is the cheapest time to stay in Chatham?
Based on historic data is usually the cheapest month to visit Chatham. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Chatham?
There are multiple hotels in Chatham that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Chatham. We have plenty of kid-friendly hotels in Chatham to choose from on Travelocity!
Why book a hotel in Chatham through Travelocity?
Because we have the top hotels in Chatham! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Chatham on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Chatham hotel reviews by fellow wanderers

Berkshires Untold

Berkshires Untold

5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"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 signal was really weak and spotty."
A verified traveler stayed at Berkshires Untold
Berkshires Untold
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