Hotels in Chatham

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Jul 17 - Jul 19
Next weekend
Jul 24 - Jul 26

Where to stay in Chatham?

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, desk, laptop workspace, blackout drapes

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,007 reviews)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is $118
$132 total
includes taxes & fees
Jul 19 - Jul 20
Best Western Plus Berkshire Hills Inn & Suites
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (491 reviews)
The price is $75
$84 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Travel Lodge
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,016 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $189
$211 total
includes taxes & fees
Jul 19 - Jul 20
The Yankee Inn
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.
The price is $75
$82 total
includes taxes & fees
Jul 19 - Jul 20
Pleasant Valley Motel West Stockbridge
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (257 reviews)
Escape to this mountain retreat with fully equipped kitchenettes and private outdoor spaces. Near Catskill Golf Club and Angelo Canna Town Park, this cabin offers free parking and climate control. Just an 18-minute drive from Hudson Station for easy regional exploration.
The price is $169
$226 total
includes taxes & fees
Jul 21 - Jul 22
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (853 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $69
$77 total
includes taxes & fees
Jul 19 - Jul 20
FairBridge Inn Express
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,014 reviews)
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
The price is $132
$148 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn Lee - Lenox South
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (135 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is $141
$157 total
includes taxes & fees
Jul 19 - Jul 20
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (18 reviews)
The price is $151
$169 total
includes taxes & fees
Jul 19 - Jul 20
Hideaway Inn Lenox
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.
The price is $190
$208 total
includes taxes & fees
Jul 20 - Jul 21
Shaker Mill Inn
Dining room

Gregory House Country Inn

Gregory House Country Inn
3.0 star property
Averill Park
9.0 out of 10, Wonderful, (112 reviews)
Experience rustic elegance at this inviting inn, where complimentary WiFi and parking enhance your stay near Pineridge Cross Country Ski Center and Berkshire Retreat Center. Unwind with a cocktail at the bar or savor a meal at the on-site restaurant.
The price is $125
$139 total
includes taxes & fees
Jul 19 - Jul 20
Gregory House Country Inn
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (885 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $99
$111 total
includes taxes & fees
Jul 19 - Jul 20
Howard Johnson by Wyndham Lenox
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, cribs (free), rollaway beds (surcharge), WiFi (free)

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (881 reviews)
The price is $124
$138 total
includes taxes & fees
Jul 20 - Jul 21
Monument Mountain Motel
Signature Apartment | Private kitchen | Shared fridge, espresso maker, coffee/tea maker, electric kettle

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (162 reviews)
This welcoming Hudson hotel offers free WiFi and rooms featuring hydromassage showerheads for ultimate relaxation. Just an 8-minute walk from the train station, you'll find cultural attractions and a hair salon on-site.
The price is $137
$154 total
includes taxes & fees
Jul 27 - Jul 28
Howard Hotel
Lake view

Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.4 out of 10, Exceptional, (6 reviews)
The price is $209
$234 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Lake Lodge
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (244 reviews)
Experience tranquil moments at this countryside retreat near Undermountain Golf Course and Copake Town Park. North Star restaurant serves American cuisine for dinner, while free WiFi and parking add convenience. Guests consistently praise the attentive staff who enhance every stay.
The price is $170
$190 total
includes taxes & fees
Jul 19 - Jul 20
the Alander
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
The price is $118
$132 total
includes taxes & fees
Aug 6 - Aug 7
Quality Inn Great Barrington
Free daily continental breakfast

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.0 out of 10, Very Good, (150 reviews)
Tucked in a peaceful area with hiking trails nearby, this hotel provides a complimentary breakfast praised by travelers. The 24-hour fitness center, free parking, and exceptionally helpful staff create a comfortable base for exploring Parks Dairy and Mcquade park.
The price is $104
$112 total
includes taxes & fees
Jul 26 - Jul 27
Spark by Hilton West Coxsackie
In-room safe, desk, cribs (free), rollaway beds (free)

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (593 reviews)
The price is $99
$111 total
includes taxes & fees
Jul 19 - Jul 20
Travelodge by Wyndham Great Barrington Berkshires
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.
View all properties

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, Hudson Chatham Winery, 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 Hudson Chatham Winery.

See all hotels in Chatham
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

Check out reviews of Chatham hotels guests love

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"It’s pretty rare for a hotel to check all of the boxes for me but this one did. Check in was friendly and efficient , room was very clean , common areas , and all areas of the hotel for that matter were clean. Was quiet , pool was heated and clean as well as hot tub. I was the only one in there the times I went which was very pleasant . Gym was clean as well. Location is right next to everything but also tucked away so you don’t that any of the main road noises. Bed was comfy. Only suggestion would be adding salt and pepper packets for breakfast :)"
Tiara 2-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

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 12 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.