Book Hotels in Chatham, NY

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Top Chatham hotels

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is $126 total per night from Nov 10 to Nov 11
$126 total
per night
Nov 10 - Nov 11
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, ...
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.

Reviewed on Nov 4, 2025

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $104 total per night from Nov 17 to Nov 18
$104 total
per night
Nov 17 - Nov 18
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby ...
Everything was clean and the staff were nice. However? I was told at check-in that rooms weren’t cleaned unless I requested it so I requested it for my 3 night stay but the room was only cleaned once.

Reviewed on Nov 4, 2025

Opens in a new windowBerkshires Untold
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St, Lee, MA
Fully refundable
The price is $122 total per night from Nov 30 to Dec 1
$122 total
per night
Nov 30 - Dec 1
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self ...
The view of the lake was great and we loked the location. The restaurant downstairs was great. The bed was hard and we didn't sleep well and the shower was horrible, the worst draining shower I've had in my life. Rooms are dated and decks could use repair.

Reviewed on Nov 7, 2025

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $113 total per night from Nov 18 to Nov 19
$113 total
per night
Nov 18 - Nov 19
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...
Staff…great Room…great We enjoy it here and stay annually

Reviewed on Nov 8, 2025

Opens in a new windowThe Yankee, Trademark Collection by Wyndham
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is $204 total per night from Nov 16 to Nov 17
$204 total
per night
Nov 16 - Nov 17
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 love the ambience - historic and comfortable and excellent food.

Reviewed on Nov 5, 2025

Opens in a new windowThe Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is $125 total per night from Nov 12 to Nov 13
$125 total
per night
Nov 12 - Nov 13
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 loved almost everything, but they need to replace sofa, armchair and the bed in this unit. Too old. The sofa and armchair have bad smell of very old furniture.

Reviewed on Nov 7, 2025

Opens in a new windowVacation Village in the Berkshires
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
The price is $117 total per night from Nov 16 to Nov 17
$117 total
per night
Nov 16 - Nov 17
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 ...
Everything was great

Reviewed on Nov 8, 2025

Opens in a new windowComfort Inn & Suites East Greenbush - Albany
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is $94 total per night from Nov 23 to Nov 24
$94 total
per night
Nov 23 - Nov 24
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. ...
The staff was amazing, so kind and accommodating. The room was clean, the beds were very comfortable. Nice breakfast options. We were in town for a concert at Mahaiwe and we didn’t use our car once we checked in… a great home base for the weekend. Will definitely be back.

Reviewed on Nov 6, 2025

Opens in a new windowQuality Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is $109 total per night from Nov 21 to Nov 22
$109 total
per night
Nov 21 - Nov 22
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public ...
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.

Reviewed on Nov 8, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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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 $94. 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 1,597 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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

5 out of 5
Posted 21 hours ago
Travelocity Verified Review
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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