Hotels in Chatham

Where to?

Dates

March 2026

13

April 2026

I'm traveling for business

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Where to stay in Chatham?

Breakfast, lunch, dinner served; American cuisine

The Old Inn On The Green

Great Barrington

Seasonal escape in historic Great Barrington with outdoor pool and fine dining.

CNY2,530 total

includes taxes & fees

Mar 15 - Mar 16

Quality Inn Lee - Lenox South

Lee

A cozy retreat 15 minutes from Tanglewood Music Center with complimentary WiFi.

CNY646 total

includes taxes & fees

Apr 6 - Apr 7

Sunset Inn

Lee

Countryside lodging with a seasonal pool, steps away from Tanglewood Music Center.

CNY729 total

includes taxes & fees

Mar 14 - Mar 15

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

Restful sanctuary in Pittsfield with free WiFi and parking, perfect for skiers.

CNY546 total

includes taxes & fees

Apr 1 - Apr 2

Chambery Inn

Lee

Peaceful countryside retreat with spa treatments just minutes from Tanglewood Music Center.

Econo Lodge Lee - Great Barrington

Lee

Cozy retreat near Lee Premium Outlets with mini golf and continental breakfast.

CNY423 total

includes taxes & fees

Apr 3 - Apr 4

Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Lee

Step back from the crowds with a relaxing Berkshires escape next to scenic fairways.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

Tranquil lakefront escape with stunning sunset views and a 24-hour fitness center.

CNY705 total

includes taxes & fees

Apr 6 - Apr 7

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

South Lee

Berkshire getaway offers indoor and outdoor pools with mountain scenery and cafe.

CNY998 total

includes taxes & fees

Mar 23 - Mar 24

Lakehouse Inn

Lee

Scenic lakeside escape in Lee with kayaking, terrace, and daily full breakfast.

CNY1,161 total

includes taxes & fees

Mar 14 - Mar 15

The Inn at Stockbridge

Lee

Unwind in the Berkshires with massages and outdoor swimming in charming Lee.

CNY1,925 total

includes taxes & fees

Mar 14 - Mar 15

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Pittsfield

Lakeside getaway in Berkshires with indoor pool and Tanglewood Music Center nearby.

CNY1,014 total

includes taxes & fees

Mar 22 - Mar 23

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Modern hotel near Herman Melville's Arrowhead with indoor pool and Asian fusion dining.

CNY982 total

includes taxes & fees

Mar 15 - Mar 16

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

Experience Lenox from a central motel with a pool and friendly staff at your service.

CNY607 total

includes taxes & fees

Mar 14 - Mar 15

Berkshire Mountain Lodge

Pittsfield

CNY970 total

includes taxes & fees

Apr 1 - Apr 2

Hampton Inn & Suites Berkshires-Lenox

Lenox

Relaxing Berkshires retreat with indoor pool near Tanglewood Music Center.

CNY854 total

includes taxes & fees

Mar 22 - Mar 23

Hotel On North

Pittsfield

Experience refined comfort in the heart of Pittsfield, steps from transportation.

CNY1,144 total

includes taxes & fees

Mar 15 - Mar 16

50-inch flat-screen TV with cable channels, TV, streaming services

The Central Downtown Inn & Suites

Pittsfield

CNY783 total

includes taxes & fees

Mar 15 - Mar 16

The Yankee, Trademark Collection by Wyndham

Lenox

Unwind in Lenox with mountain vistas, seasonal pools, and easy Berkshire access.

CNY711 total

includes taxes & fees

Mar 22 - Mar 23

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Located in Pittsfield, the hotel offers peaceful rooms near Berkshire attractions.

CNY940 total

includes taxes & fees

Mar 14 - Mar 15

View all properties

Go beyond your typical stay in Chatham

Family friendly

Pet friendly

Top landmarks in Chatham

The Mac-Haydn Theatre

The Mac-Haydn Theatre is 0.9 mi (1.4 km) from central Chatham, why not stop by during your stay. If you want to experience more of the culture Chatham has to offer, head to Art Omi International Arts Center - Fields Sculpture Park, Van Alen House, and Martin Van Buren National Historic Site.

See properties

Learn more about Chatham

The region around Chatham is home to attractions such as The Mac-Haydn Theatre and Van Alen House.

See all hotels in Chatham

Tracy Memorial Village Hall, Chatham, New York

Check out reviews of Chatham hotels guests love

Berkshires Untold

8/10 Good

"Room was clean. Redone motel"

Four Points by Sheraton Albany

10/10 Excellent

"This is a review for a stay that was booked for Sunday night, Feb 28 th. As it happened my friend became too ill for us to visit and the trip was cancelled. Notified 4 Points on Saturday why I needed to cancel. I was told since I booked through Expedia my request was not in Sheraton’s hands but Expedia. Expedia was willing to credit as long as 4 points agreed. Since 4 points didn’t respond to Expedia, my request was turned down. I was surprised since this stay would have been my 3rd time to book a room with Four Points by Sheraton Albany. Too bad, there are future visits in the planning but not with Four Points Albany for me. "

Frequently asked questions

How much does a hotel room cost in Chatham?

You can choose a great hotel in Chatham from CNY423 with properties to suit all budgets and needs. If you're after an affordable hotel in Chatham that meets all of your requirements, set your filters and then sort the results by "Price: low to high".

How can I find deals and earn rewards at Chatham hotels?

Discover great deals on Chatham hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Chatham hotels.

Can I book Chatham hotels with free cancellation?

To book a refundable Chatham hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Most hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

Can I book a refundable hotel in Chatham?

If you want the flexibility to change your plans to Chatham, most accommodations offer refundable* rates you can book. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Chatham if I want a vacation rental instead of a hotel?

If you want to find a good alternative to a hotel, review our selection of 14 vacation homes.

What will the weather in Chatham be like during my vacation?

July and August are typically the warmest months in Chatham when the average temp is 67°F. January and February are the coldest months when the average temperature is 29°F. October and August are the months with the most rain.

Why should I book my Chatham accommodation with Hotels.com?

There are lots of reasons to book your Chatham trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Keep exploring

Book Hotels in Chatham on Hotels.com