Chatham Hotels from S$92

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
20 Jul - 21 Jul
Tomorrow
21 Jul - 22 Jul
Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Chatham hotels

The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is S$450
includes taxes & fees
22 Jul - 23 Jul
The Old Inn On The Green
Pilgrim Inn
Enjoy meals in the dining area with a round table and comfortable seating.

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is S$115
includes taxes & fees
3 Aug - 4 Aug
Pilgrim Inn
Quality Inn
Welcome to our reception area, featuring a comfortable seating space with a fireplace, flat-screen TV, and stunning views of the outside.

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Friendly staff, easy parking"
The price is S$194
includes taxes & fees
4 Aug - 5 Aug
Quality Inn
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (392)
"No frills but it was a great stay!"
The price is S$150
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
FairBridge Inn Express
Relax in a spacious room with a large bed, two bedside tables, and a separate bathtub area.

FairBridge Inn Express

2.5 star property
5.4 out of 10, (749)
"Close to our target event a plus"
The price is S$102
includes taxes & fees
3 Aug - 4 Aug
FairBridge Inn Express
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Econo Lodge Lee - Great Barrington
Relax in comfort with a large bed, two bedside tables, and a balcony with a view.

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (611)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is S$92
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Black Swan Lee - Lenox, Ascend Hotel Collection
Relax in a serene lakeside setting with Adirondack chairs and a tranquil atmosphere.

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful location!"
The price is S$279
includes taxes & fees
30 Jul - 31 Jul
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Play a round of golf amidst lush surroundings and scenic obstacles.

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

3.5 star property
9.0 out of 10, Wonderful, (678)
"Terrific place. Spacious, clean, comfortable."
The price is S$255
includes taxes & fees
23 Jul - 24 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Enjoy a diverse selection of hot and cold dishes at our buffet.

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is S$255
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is S$275
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Enjoy a serene outdoor setting with two picnic tables on a well-maintained lawn.

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (611)
"Convenient location for my trip"
The price is S$99
includes taxes & fees
22 Jul - 23 Jul
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Stylish motel with a central entrance and two wings, featuring individual rooms with doors and windows.

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (762)
"Was great loved the jacuzzi tub "
The price is S$142
includes taxes & fees
22 Jul - 23 Jul
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and gas range.

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (523)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Hotel features a two-story design with a flat roof and a mix of brick and siding.

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Good lodgings in a great area to visit."
The price is S$231
includes taxes & fees
30 Jul - 31 Jul
Hampton Inn & Suites Berkshires-Lenox
Hotel On North
Enjoy a diverse menu at this restaurant, featuring a selection of drinks and a modern design.

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (745)
"Great boutique hotel"
The price is S$271
includes taxes & fees
27 Jul - 28 Jul
Hotel On North
The Yankee, Trademark Collection by Wyndham
Classic hotel entrance with a covered walkway, surrounded by beautifully maintained gardens.

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Loved the Yankee Inn!"
The price is S$194
includes taxes & fees
30 Jul - 31 Jul
The Yankee, Trademark Collection by Wyndham
The Central Downtown Inn & Suites
Compact kitchen with modern design, featuring white and wood cabinetry, refrigerator, coffee maker, and toaster.

The Central Downtown Inn & Suites

4.0 star property
8.8 out of 10, Excellent, (298)
"Friendly staff, clean and perfect for a trip with the pups! "
The price is S$185
includes taxes & fees
22 Jul - 23 Jul
The Central Downtown Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (825)
"Very convenient location, downtown, short drive to local attractions "
The price is S$185
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Chatham

Escape to Chatham! Enjoy its theatre and dining.

See all hotels in Chatham

Top Chatham Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"We enjoyed the unique character and flavor of the hotel!"
Brad 3-night trip
Posted 2 days ago
Berkshires Untold

Frequently asked questions

What's the best place to stay in Chatham?

Located 20.8 mi (33.5 km) from the heart of Chatham, Vacation Village in the Berkshires is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Berkshires Untold and Best Western Plus Berkshire Hills Inn & Suites. See all available top hotels, or vacation rentals in Chatham.

If I need to cancel my hotel reservation in Chatham, will I receive a refund?

Yes! Most hotel room reservations are refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chatham.

What are some accommodation options with pools in Chatham?

Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and Holiday Inn & Suites Pittsfield-Berkshires by IHG are a couple of other choices that feature an on-site pool. View all hotels with pools in Chatham.

What is staying in Chatham like?

Visitors can enjoy all that Chatham has to offer, including the theatres and restaurants. This city also attracts tourists with its welcoming locals. In Chatham, there are 24 hotels and other accommodation options to choose from. Find out more about Chatham.

What are the top places to visit in Chatham?

A favourite place to visit is The Mac-Haydn Theatre. You'll also find Martin Van Buren National Historic Site and Kinderhook Lake in the area. Take a look at what more there is to see and do in Expedia's Chatham guide.

What's the seasonal weather in Chatham?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm of snowfall.