Book Hotels in Chatham, New York

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Most frequently booked Chatham hotels

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

16.92 mi from city center

$115

per night

Oct 5 - Oct 6

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 the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Comfort Inn Glenmont - Albany South

37 Route 9W, Glenmont, NY

Free Cancellation

Reserve now, pay when you stay

20.11 mi from city center

$104

per night

Oct 1 - Oct 2

A full-service spa, an indoor pool, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like full breakfast and free self parking.

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Williamstown, MA

Free Cancellation

Reserve now, pay when you stay

20.8 mi from city center

$169

per night

Sep 29 - Sep 30

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 like free self parking and free WiFi.

The Red Lion Inn

30 Main Street, Stockbridge, MA

15.52 mi from city center

Get rates

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and concierge services.

Life House Berkshires

194 Pittsfield Rd, Lenox, MA

16.47 mi from city center

$164

per night

Oct 29 - Oct 30

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. Express check-in is provided and the front desk is staffed around-the-clock.

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock, MA

20.4 mi from city center

$139

per night

Oct 15 - Oct 16

Ski-in/ski-out access, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free condo resort. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Seven Hills Inn

40 Plunkett Street, Lenox, MA

Free Cancellation

Reserve now, pay when you stay

16.18 mi from city center

$127

per night

Oct 2 - Oct 3

This hotel features free WiFi in public areas, concierge services, and free self parking. Enjoy the free on-the-go breakfast each morning. A terrace, a garden, and a library are also on offer.

James Newbury Hotel

60 S River St, Coxsackie, NY

Free Cancellation

Reserve now, pay when you stay

10.24 mi from city center

$141

per night

Oct 17 - Oct 18

A full-service spa and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. The front desk is staffed around-the-clock and concierge services are on offer.

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St, Pittsfield, MA

15.22 mi from city center

$114

per night

Oct 22 - Oct 23

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 24-hour business center, express check-out, and conference space. There's a gym on site, and laundry facilities and free newspapers are also offered.

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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.

Top family friendly Chatham hotel deals

Chatham Travel Lodge

598 NY-295, Old Chatham, NY

$100

per night

Oct 1 - Oct 2

7/10 Good! (113 reviews)

Top hotels in Chatham for Extended Stay

Micosta Leisure Inn

3007 County Rd 20, Hudson, NY

$125

per night

Oct 1 - Oct 2

9/10 Wonderful! (60 reviews)

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.

Chatham hotels essential information

Accommodation	1,403 hotels
Lowest Price	$100
Highest Price	$169
Popular hotels	The Yankee, Trademark Collection by Wyndham, Comfort Inn Glenmont - Albany South, Vacation Village in the Berkshires, The Red Lion Inn, Life House Berkshires, Jiminy Peak Mountain Resort, Seven Hills Inn, James Newbury Hotel, Best Western Plus Berkshire Hills Inn & Suites

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: Cozyhot tubfire 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 $100. 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 1,403 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.