Chatham hotels from RM365

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Chatham hotels

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
Located minutes from Tanglewood Music Centre, this Lenox hotel offers an indoor pool, bar, and free parking. Grab coffee at the café before exploring nearby Kennedy Park. Business travellers will appreciate the free WiFi and convenient amenities.

"Rooms were very clean and spacious."
United States
Morgan
The price is RM547
RM611 total
includes taxes & fees
4 Jan - 5 Jan 2026
Element Lenox Berkshires

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, (1001)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness centre or enjoy nearby skiing options. Tanglewood Music Centre and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.

"Very friendly and good Breakfast."
United States
Jesse
The price is RM309
RM346 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1003)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transport Centre, this hotel offers peaceful accommodation with an indoor pool. Enjoy the fitness centre, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theatre.

"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is RM357
RM399 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodation include refrigerators and microwaves. Unwind in the hot tub, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.

"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is RM410
RM458 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Yankee, Trademark Collection by Wyndham

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (117)
Escape to tranquil Catskill cabins featuring convenient kitchenettes and private furnished patios. Just minutes from Catskill Golf Club and Angelo Canna Town Park, with free parking and Hudson Station only 18 minutes away.

"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is RM522
RM739 total
includes taxes & fees
6 Jan - 7 Jan 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very good, (985)
Located near Parks Dairy and Bronck Island, this welcoming hotel offers free breakfast and complimentary WiFi. Enjoy the 24-hour fitness centre after a day of local exploration or snowboarding. Guests consistently praise the helpful staff and morning meal.

"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
The price is RM336
RM363 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1000)
Set in a serene location near Housatonic River Walk, this hotel offers free breakfast, WiFi, and parking. Enjoy the fitness centre or explore nearby trails for hiking and skiing. Guests praise the helpful staff and quiet atmosphere in this convenient Great Barrington retreat.

"My go to place for my ski weekends"
United States
Ryan
The price is RM306
RM342 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Great Barrington

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (439)
Tucked in West Stockbridge, this charming B&B offers complimentary morning meals and convenient self parking. Outdoor enthusiasts can explore nearby hiking trails, kayaking spots, and mountain biking routes. Ebenezer II Gifts and Hotchkiss Mobile Studio await just minutes away.

"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is RM482
RM529 total
includes taxes & fees
6 Jan - 7 Jan 2026
Shaker Mill Inn

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.

"Staff was very friendly and helpful."
United States
Pamela
The price is RM320
RM357 total
includes taxes & fees
30 Dec - 31 Dec
Howard Johnson by Wyndham Lenox

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1001)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Centre. After working out in the 24-hour fitness centre, savour Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.

"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is RM421
RM470 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
Located in Lee, this inviting B&B offers kayaking adventures and a terrace with lakefront views. Wake up to a full breakfast each morning before exploring nearby attractions like The Mount and Wyndhurst Golf & Club. Helpful staff ensure a memorable stay.

"A charming inn in the center of the Berkshires."
United States
Danny
The price is RM693
RM812 total
includes taxes & fees
30 Dec - 31 Dec
Lakehouse Inn

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (796)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.

"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is RM400
RM537 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
Explore Berkshire County from this Pittsfield hotel featuring an indoor pool and fitness centre. Enjoy meals at Jae's Asian Fusion restaurant and bar, plus in-room refrigerators and microwaves. Nearby attractions include Herman Melville's Arrowhead and Guido's Marketplace.

"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is RM518
RM579 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Lenox Pittsfield

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (17)
Discover a tranquil Great Barrington escape with an outdoor pool and rejuvenating sauna. Enjoy dinner at The Cliff House featuring local cuisine, then unwind at the bar. Near Catamount Aerial Adventure Park with free WiFi and parking for easy exploration.

"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is RM1,021
RM1,276 total
includes taxes & fees
26 Jan - 27 Jan 2026
Prospect Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (713)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness centre, and complimentary WiFi.

"We stay here every year and it never disappoints "
United States
Elizabeth
The price is RM413
RM461 total
includes taxes & fees
28 Jan - 29 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1001)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Centre. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.

"Safe, clean rooms, decent breakfast "
United States
Neil
The price is RM341
RM381 total
includes taxes & fees
11 Jan - 12 Jan 2026
Quality Inn Lee - Lenox South

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is RM603
RM855 total
includes taxes & fees
26 Jan - 27 Jan 2026
The Red Lion Inn

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (348)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is RM381
RM425 total
includes taxes & fees
30 Dec - 31 Dec
The Central Downtown Inn & Suites

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
This peaceful motel offers a seasonal outdoor pool and clean rooms just 15 minutes from Tanglewood Music Centre. Close to Colonial Theatre and Berkshire Museum, with free WiFi and parking. Guests praise the helpful staff and quiet, relaxing atmosphere.

"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is RM348
RM389 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Inn
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

Stay near popular Chatham attractions

Learn more about Chatham

This charming upstate village hosts the Mac-Haydn Theatre's summer productions and a vibrant Main Street with independent shops and cafés. Explore the historic Union Station or time your visit for the Columbia County Fair, a beloved local tradition since 1841.

Tracy Memorial Village Hall, Chatham, New York

Top Chatham Hotel Reviews

More cheap stays in Chatham

Find out more about Chatham

Top reasons to visit Chatham

  • Outdoor Adventures: Chatham is perfect for skiing, hiking, and exploring picturesque lakes, ideal for nature enthusiasts.
  • Charming City Centre: Stroll through the lovely city centre, where friendly locals create a welcoming atmosphere.
  • Rich History: Immerse yourself in the region’s history with visits to historic sites and local theatre performances.
  • Relaxing Getaways: Enjoy tranquil beach escapes and scenic countryside perfect for unwinding.
  • Diverse Accommodations: Choose from quaint agritourism properties and inviting bed & breakfasts tailored to all travellers.

Find great hotels near Chatham

Experience the charm of Chatham, New York, with an array of delightful lodging options, including quaint agritourism properties and inviting bed & breakfasts. Whether you're seeking a pet-friendly retreat or an adventure-filled family vacation, the region offers a variety of accommodations tailored to your needs. From cosy abba hotels to modern AC hotels, you'll find the perfect base to explore the beauty of this picturesque area.

  • The Red Lion Inn: Experience the charm of history at The Red Lion Inn, a 3.5-star hotel located merely 25.7km from Chatham. Set within a national historic building, this accommodation is perfect for those seeking a blend of adventure and business travel. Guests can indulge in a range of onsite or nearby recreation activities, including mountain biking, snowboarding, and snowshoeing. The inn's unique historic theme is complemented by comfortable rooms and a welcoming atmosphere, making it an ideal base for your adventures.
  • St. Charles Hotel: Located just 20.9km from Chatham, St. Charles Hotel offers a warm and inviting environment for pet lovers. With a pet-friendly policy that permits dogs and cats, this hotel ensures that your furry companions are welcome. Guests appreciate the amenities that cater to pets, including a waived fee for service animals. The hotel's relaxed atmosphere and convenient location make it an excellent choice for travellers seeking comfort and companionship during their stay.
  • The Little Lion: A delightful 3-star motel situated 25.7km from Chatham, The Little Lion caters to pet owners looking for a friendly and accommodating stay. With a pet-friendly policy that includes free permits for pets, this establishment prioritises the comfort of all guests, including those with four-legged friends. The motel offers a cosy environment, ensuring a pleasant and enjoyable experience for both you and your pets while exploring the beautiful surroundings.

Where to stay near Chatham

Chatham, New York, offers a delightful blend of outdoor adventures and romantic escapes. Wander through the charming city centre, where friendly locals create a warm atmosphere. Explore the beautiful countryside, perfect for a relaxing getaway, or delve into the region's rich history. Nearby attractions provide family-friendly experiences and budget options, making it an inclusive destination for all travellers seeking picturesque scenery and memorable moments.

  • Hudson: A vibrant city located 20.9km from Chatham, Hudson is a haven for outdoor enthusiasts and adventure seekers. The city is particularly bustling from July to September, offering a range of activities like skiing at local resorts and exploring the scenic lakes and mountains. Visitors can immerse themselves in the natural beauty of the area while enjoying the lively tourist precinct, where local shops and eateries abound. Whether you're looking to hit the slopes or simply appreciate the picturesque landscape, Hudson promises a memorable experience.
  • Old Chatham: Situated a mere 9.7km from Chatham, Old Chatham is a charming city that captivates visitors with its romantic atmosphere and outdoor adventures. The peak travel season from June to August draws those eager for cultural experiences, such as music concerts and theatre performances. The area also boasts beautiful lakes and historic civic buildings, providing a unique backdrop for exploration. Perfect for couples looking to enjoy a delightful getaway or families seeking adventure, Old Chatham offers an enchanting blend of activities and sights.
  • Austerlitz: Just 12.9km away from Chatham, Austerlitz is an outdoor paradise ideal for families and adventure lovers. The city sees its visitor numbers peak during the warmer months of June to July and September, making it a popular spot for skiing and theatre events. With stunning lakes, majestic mountains, and historic buildings nearby, Austerlitz invites you to engage with its rich heritage while enjoying various recreational activities. It's a fantastic destination for a fun-filled family holiday or an adventurous weekend escape.

Things to do in and around Chatham

Chatham offers a delightful blend of outdoor adventure and romantic escapades, making it an ideal vacation spot. Visitors can enjoy skiing at nearby ski fields and immerse themselves in local theatre performances. For those seeking relaxation, a beach getaway is perfect, while night trips provide a unique way to explore the area's charm under the stars. Whether you’re after thrills or tranquility, Chatham has something to satisfy every traveller's desire.

Shopping

In Chatham, you can explore unique gifts at local favourites like Hoffman's Pottery, Charles H. Baldwin & Sons, and Stoddard Corner, all located 19.3km away. If you're up for a drive, these charming stores offer delightful souvenirs and handcrafted items to bring home.

Recreation

Experience the enchanting Tanglewood Music Center, a mere 24.1km from Chatham, where you can immerse yourself in captivating concerts. For a tranquil retreat, visit Fairfield Brook WMA, 20.9km away, and enjoy its serene nature. Additionally, Mosher Park, located 22.5km from Chatham, offers a peaceful environment for relaxation.

Adventure

Experience the thrill at Catamount Ski Area, a ski field 24.1km from Chatham, perfect for snow sports enthusiasts. Hike the scenic High Falls Trail, located 14.5km away, for stunning views and outdoor adventure. For more excitement, try the Catamount Aerial Adventure Park, 22.5km away, featuring ziplines and ropes courses.

Nightlife

Experience the charm of Chatham's nightlife at The Mac-Haydn Theatre, where romance and culture come alive. For a short drive, visit the Max and Lillian Katzman Theater and Shakespeare and Company, both offering captivating performances just a stone's throw away, enhancing your evening with artistic flair.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chatham

To save money on your trip to Chatham, New York, consider visiting in March or December to January when accommodation prices are lower. Mondays are the most budget-friendly days to stay, while Saturdays tend to be pricier. Utilise Expedia’s search tool to filter by budget and find the best deals on hotels. Combining your hotel booking with flights and activities through an Expedia package can also yield savings. Keep an eye out for available offers and cheap hotel deals to maximise your budget.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chatham are March and December to January, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chatham is Monday. The most expensive day to stay in Chatham is Saturday.
  • Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, desired location, and preferred type of accommodation. To find the most affordable prices and deals, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save some money by combining your Chatham hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Chatham

Chatham, New York, offers a delightful blend of outdoor adventures and romantic experiences. Visitors can explore picturesque lakes and historic sites, while the local library provides a charming cultural retreat. With a variety of attractions catering to families and nature enthusiasts alike, Chatham is an ideal destination for those seeking a memorable getaway filled with both adventure and relaxation.

  • Hancock Shaker Village: Immerse yourself in the unique culture of the Shakers at this historic village, showcasing beautifully preserved buildings and traditional crafts. Experience the serene beauty of the landscape while learning about sustainable practices and communal living.
  • Hudson Opera House: This vibrant arts centre is a cultural hub featuring a variety of performances and exhibitions. Enjoy the stunning architecture and explore diverse art forms, making it a must-visit for art enthusiasts.
  • Martin Van Buren National Historic Site: Delve into American history at the former home of the eighth president. The site offers guided tours and exhibits that highlight Van Buren's life and legacy, set amidst picturesque grounds.

Best time to go to Chatham

The best time to visit Chatham can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chatham falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chatham falls in January, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudyAverageSlightly Low
February26.2°F (-3.2°C)Light RainMostly CloudyAverageAverage
March34.2°F (1.2°C)Light RainMostly CloudyAverageSlightly Low
April45.7°F (7.6°C)Light RainMostly CloudyAverageAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June65.3°F (18.5°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighAverage
October51.4°F (10.8°C)Light RainMostly SunnySlightly LowSlightly High
November39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly Low

The nearest major airports for your trip to Chatham

When planning your visit to Chatham, New York, you have several airport options. Hartford, CT (BDL-Bradley International) is situated 88.5km away, with nearby hotels like the 4-star Simsbury 1820 House and Marriott Hartford Downtown. Albany, NY (ALB-Albany International) is 46.7km away, offering accommodations such as The Landing Hotel at Rivers Casino & Resort and Hilton Garden Inn Albany Medical Center. The closest airport is Hudson, NY (HCC-Columbia County), located 12.9km away, with options like The Nest Hudson and Hudson City Bed & Breakfast. Each airport provides convenient access to local hotels for a comfortable stay.

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 Comfort Inn Glenmont - Albany South and The Yankee, Trademark Collection by Wyndham. 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. Comfort Inn Glenmont - Albany South and The Yankee, Trademark Collection by Wyndham 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 25 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.

Explore a world of travel with Expedia