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Check prices for these dates

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12 Aug - 13 Aug
Tomorrow
13 Aug - 14 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

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Our top choices for Chatham hotels

1. Gatherwild Ranch

Gatherwild Ranch
Germantown
SAR 801
SAR 897 total
includes taxes & fees
26 Aug - 27 Aug
Gatherwild Ranch

2. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
United States
Rita
SAR 589
SAR 658 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Lake Lodge

3. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
SAR 1,197
SAR 1,444 total
includes taxes & fees
1 Sep - 2 Sep
The Old Inn On The Green

4. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
Lee
United States
Christine
SAR 402
SAR 449 total
includes taxes & fees
31 Aug - 1 Sep
Quality Inn Lee - Lenox South

5. Sunset Inn

Sunset Inn
Lee
Canada
Kevin
SAR 357
SAR 399 total
includes taxes & fees
1 Sep - 2 Sep
Sunset Inn

6. FairBridge Inn Express

FairBridge Inn Express
Pittsfield
United States
Christian
SAR 222
SAR 247 total
includes taxes & fees
31 Aug - 1 Sep
FairBridge Inn Express

7. Chambery Inn

Chambery Inn
Lee
United States
Joseph
SAR 1,014
SAR 1,132 total
includes taxes & fees
13 Aug - 14 Aug
Chambery Inn

8. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Lynne
SAR 252
SAR 282 total
includes taxes & fees
7 Sep - 8 Sep
Econo Lodge Lee - Great Barrington

9. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Richard
SAR 1,461
SAR 1,631 total
includes taxes & fees
3 Sep - 4 Sep
Devonfield Inn B&B

10. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
James
SAR 504
SAR 563 total
includes taxes & fees
8 Sep - 9 Sep
The Black Swan Lee - Lenox, an Ascend Collection Hotel

11. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
United States
Marc
SAR 402
SAR 523 total
includes taxes & fees
10 Sep - 11 Sep
Holiday Inn Club Vacations Oak 'n Spruce Resort

12. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
United Kingdom
Michele
SAR 1,507
SAR 1,768 total
includes taxes & fees
7 Sep - 8 Sep
The Inn at Stockbridge

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
United States
Ken
SAR 492
SAR 549 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

14. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
United States
Adeline
SAR 618
SAR 691 total
includes taxes & fees
10 Sep - 11 Sep
Hilton Garden Inn Lenox Pittsfield

15. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
United States
Luciane
SAR 297
SAR 331 total
includes taxes & fees
31 Aug - 1 Sep
Howard Johnson by Wyndham Lenox

16. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
United States
Andrea
SAR 355
SAR 481 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge

17. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
United States
Nancy
SAR 551
SAR 616 total
includes taxes & fees
31 Aug - 1 Sep
Hampton Inn & Suites Berkshires-Lenox

18. Hotel On North

Hotel On North
Pittsfield
United States
Dragana
SAR 672
SAR 751 total
includes taxes & fees
7 Sep - 8 Sep
Hotel On North

19. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
United States
Rena
SAR 342
SAR 382 total
includes taxes & fees
3 Sep - 4 Sep
The Central Downtown Inn & Suites

20. The Yankee Inn

The Yankee Inn
Lenox
United States
Larry
SAR 620
SAR 692 total
includes taxes & fees
7 Sep - 8 Sep
The Yankee Inn
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Stay near popular Chatham attractions

The Mac-Haydn Theatre

This intimate theater-in-the-round presents professional summer musicals with New York City talent. Every seat offers an immersive view of the dynamic performances, running from Memorial Day through Labor Day.
See properties

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.

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

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Thus was a quick over night for us but we will be back. There was allt of bang for your buck, outside pool with grills to use plenty for the little people to do, also has an inside pool with a huge hot tub. The room was absolutely amazing. Dont hesitate on booking here, we'll worth it"
David 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
voco James Newbury Hudson Valley by IHG

voco James Newbury Hudson Valley by IHG

8/10 Good
"Stayed one night. Hotel was beautifully situated by the Hudson river and landscape was amazing and well maintained. Room was clean and staffs were friendly. But not quite recommend their breakfast."
Hee 1-night trip
Posted 5 hours ago
voco James Newbury Hudson Valley by IHG
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8/10 Good
"nice lobby and in house movie night. Room is so spacious, larger than expected with separate bedroom which is very nice. some peeling of paint on walls and bathroom fan did not work but otherwise great room, wish they offered a free breakfast or treats in lobby, but free coffee and tea in lobby was nice"
Jennifer 2-night trip
Posted 6 hours ago
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

8/10 Good
"Good location and value during the high season when prices are sky high in the area. Breakfast is handy although options are limited. All day coffee in the lobby is a plus."
Karen 2-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Lucy 2-night trip
Posted 2 days ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Quiet and serene. Great weekend escape!"
Christopher 2-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

8/10 Good
"Great stay. Very easy and affordable. No issues."
James 1-night trip
Posted 2 days ago
Comfort Inn & Suites East Greenbush - Albany
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"For a non-chain hotel, I was pleasantly surprised. Clean and comfortable. But definitely a B- C+ place which was perfect for a quick stay."
Susan 1-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Parking"
Wilson 1-night trip
Posted 10 days ago
Howard Johnson by Wyndham Lenox

More cheap stays in Chatham

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
SAR 222
SAR 247 total
31 Aug - 1 Sep
includes taxes & fees
5.4/10 (869 reviews)
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
SAR 348
SAR 389 total
2 Sep - 3 Sep
includes taxes & fees
Quality Inn Great Barrington
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY
SAR 403
SAR 462 total
23 Aug - 24 Aug
includes taxes & fees
Country Inn & Suites by Radisson, Downtown Albany New York
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

99 Miller Rd Castleton-on-Hudson NY
SAR 428
SAR 475 total
7 Sep - 8 Sep
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Comfort Inn & Suites East Greenbush - Albany
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

1055 South Street Pittsfield MA
SAR 492
SAR 549 total
7 Sep - 8 Sep
includes taxes & fees
9.4/10 Exceptional! (157 reviews)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
SAR 620
SAR 692 total
7 Sep - 8 Sep
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
The Yankee Inn

Find out more about Chatham

Top reasons to visit Chatham

  • Outdoor Adventures: Chatham is a haven for outdoor enthusiasts, offering skiing, hiking, and fishing in picturesque landscapes.
  • Charming Downtown: Explore the quaint downtown area filled with friendly locals and cozy cottages that create a welcoming atmosphere.
  • Cultural Experiences: Enjoy the local theater scene and discover historic sites that reflect the town's rich heritage.
  • Romantic Getaways: Perfect for couples, Chatham provides a romantic setting for relaxation and adventure alike.
  • Cozy Accommodations: Choose from a variety of inviting lodgings including bed and breakfasts and agritourism properties.

Find great hotels near Chatham

Discover the charm of Chatham, New York, with a variety of cozy accommodations perfect for every traveler. From agritourism properties to inviting bed and breakfasts, you'll find options that cater to pet-friendly adventures and family vacations. Explore the best hotels in Chatham, read reviews, and find competitive room rates to ensure a memorable stay in this picturesque town.

  • Best Western Plus Berkshire Hills Inn & Suites: Nestled 24.1km from Chatham, the Best Western Plus Berkshire Hills Inn & Suites offers a welcoming atmosphere for families, business travelers, and pet owners alike. This hotel is uniquely positioned to cater to the needs of children, featuring amenities such as a First Aid Kit, games, and cribs available for a fee. Pet lovers will appreciate the pet-friendly policy, which includes a dog exercise area and waives fees for service animals, ensuring a comfortable stay for all members of the family.
  • Comfort Inn & Suites East Greenbush - Albany: Located 25.7km from Chatham, the Comfort Inn & Suites East Greenbush - Albany is a convenient choice for both business and leisure travelers. With its pet-friendly environment, the hotel welcomes dogs and cats, ensuring that your furry companions can join the adventure. Guests can enjoy a range of amenities designed to enhance their stay, including complimentary breakfast and a fitness center. The commitment to providing a comfortable and accommodating experience makes this hotel a popular choice among those visiting the area.
  • Spark by Hilton West Coxsackie: Just 19.3km from Chatham, Spark by Hilton West Coxsackie is a modern hotel that combines a vibrant atmosphere with family-friendly amenities. Ideal for those traveling with children and pets, it offers cribs for a fee and allows pets in rooms, making it a stress-free option for families on the go. Guests can enjoy a range of facilities designed for both relaxation and productivity, ensuring a pleasant stay for everyone. The hotel's contemporary design and warm hospitality create an inviting environment that enhances any visit.

Where to stay near Chatham

Chatham, New York, offers a delightful blend of outdoor adventures and romantic getaways. Explore the charming downtown area, where friendly locals and cozy cottages create a welcoming atmosphere. Venture into nearby regions for breathtaking views and family-friendly activities. Whether you’re seeking a memorable vacation filled with relaxation or an exciting escape, Chatham's unique vibe ensures an unforgettable experience for every traveler.

  • Ghent: Nestled just 4.8km from Chatham, Ghent is a charming city that offers a delightful blend of outdoor activities and romantic scenery. Visitors flock to this picturesque area to enjoy its beautiful landscapes, including lakes and mountains. Popular activities include skiing at the nearby ski resorts, making it a year-round destination for adventure enthusiasts. Whether you’re looking for a relaxing day at the park or a thrilling outdoor experience, Ghent has something for everyone.
  • Hudson: Approximately 14.8km from Chatham, Hudson is a vibrant city known for its adventurous spirit. With its stunning backdrop of lakes and mountains, Hudson attracts travelers seeking outdoor adventures, especially skiing in the winter months. The city also boasts a lively tourist precinct with shops, dining, and cultural experiences. Peak visitor seasons from July to September promise a bustling atmosphere, making it an ideal spot for those looking to immerse themselves in the local vibe while enjoying thrilling outdoor activities.
  • East Chatham: Located 8.0km from Chatham, East Chatham is a quaint city that offers a perfect blend of adventure and cultural experiences. Known for its music concerts and theater events, this area is a haven for art lovers. Outdoor enthusiasts can also enjoy skiing and the picturesque landscapes that feature lakes and mountains. With peak travel seasons in June, July, and September, East Chatham invites visitors to explore its rich history and vibrant community while engaging in exciting outdoor activities.

Things to do in and around Chatham

Chatham, New York, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy skiing in the picturesque snow-covered landscapes and experience the local theater scene. As night falls, Chatham offers a charming nightlife experience, making it an ideal destination for adventure and relaxation alike.

Shopping

In Chatham, you can explore local shops like Hoffman's Pottery, Charles H. Baldwin & Sons, and Stoddard Corner, all located 19.3km away. If you're up for a drive, these stores offer unique gifts and souvenirs that capture the charm of the area.

Recreation

At Tanglewood Music Center, enjoy captivating concerts in a vibrant atmosphere that uplifts the spirit. Lake Mansfield Park offers serene trails and tranquil waters, perfect for relaxation and rejuvenation. Kennedy Park features beautiful green spaces, ideal for leisurely strolls and connecting with nature.

Adventure

At Catamount Ski Area, 24.1km from Chatham, enjoy skiing and thrilling winter sports amidst a vibrant atmosphere. High Falls Trail, 14.5km away, invites you to hike through stunning scenery and embrace the great outdoors. Experience excitement at Catamount Aerial Adventure Park, 22.5km from Chatham, with exhilarating ziplining and ropes courses.

Nightlife

Chatham’s nightlife offers a charming experience with venues like The Mac-Haydn Theatre, showcasing local talent and culture. For a short drive, enjoy performances at Max and Lillian Katzman Theater or Shakespeare and Company, both steeped in romance and entertainment, creating memorable evenings.

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

Booking tips and Expedia advantages for Chatham

For a budget-friendly trip to Chatham, New York, consider visiting during the off-peak months of March and December to January for lower accommodation rates. Mondays tend to be the cheapest days to stay, while Saturdays are pricier. Use Expedia to compare hotel prices, and filter for eco-certified options to find affordable, sustainable stays. Save even more by bundling your hotel, flights, and activities in a package deal. Take advantage of beverage discounts and special offers, and explore free local attractions to enhance your experience without breaking the bank.

  • 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and the type of hotel you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Chatham with your flights and activities through an Expedia package deal.

Find the best attractions near Chatham

Chatham offers a charming blend of outdoor adventures and romantic getaways, perfect for travelers seeking culture and family experiences. Explore the picturesque lakes, visit historic sites, or relax at the local library. Whether you're hiking, fishing, or simply enjoying the scenic beauty, Chatham's attractions provide a delightful escape into nature and history.

  • Martin Van Buren National Historic Site: This historic site, located 9.7km from Chatham, offers a glimpse into the life of the eighth President of the United States. Explore the beautifully preserved home and grounds, immersing yourself in the rich culture and history of early 19th-century America.
  • Art Omi International Arts Center - Fields Sculpture Park: Situated 6.4km from Chatham, this outdoor sculpture park is perfect for families. Wander through stunning landscapes adorned with contemporary sculptures, engaging with art in a natural setting that fosters creativity and inspiration.
  • Shaker Museum and Library: Located 8.0km from Chatham, this museum showcases the unique culture of the Shaker community. Discover their remarkable craftsmanship, innovative design, and spiritual beliefs through engaging exhibits and a vast library.

Best time to go to Chatham

The best time to visit Chatham is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

For your vacation in Chatham, New York, you can fly into several nearby airports. Hartford, CT (BDL-Bradley Intl.) is about 88.5km away, with hotel options like the 4-star DoubleTree by Hilton Hartford - Bradley Airport, just 1.6km from the airport. ALBany, NY (ALB-Albany Intl.) is 46.7km away, featuring the 4-star Park Manor Hotel, located 12.9km from the airport. The closest option is Hudson, NY (HCC-Columbia County), only 12.9km away, with hotels like The Wick, Hudson, a 4-star hotel just 8.0km from the airport, offering shuttle services. Each airport has convenient access to various 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 traveler data. Other good options for your trip to the area are Country Inn & Suites by Radisson, Downtown Albany New York and The Yankee Inn. See all available top hotels, or vacation rentals in Chatham.
What are some of the best vacation home rentals in Chatham?
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: Visitors like this Chatham vacation home rental. It is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. See all vacation rentals in Chatham.
If I need to cancel my hotel reservation in Chatham, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable as long as you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might still have the option to cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chatham.
Where can I learn more about changing or cancelling my trip to Chatham?
To access more information about rescheduling or cancelling your trip to Chatham, head over to our customer service page.
Where is the best place to stay close to The Mac-Haydn Theatre?
Charming Farm House on 460 Acre Working Farm is one of the top choices for your stay based on our traveler data, and this property features in-room kitchens and private patios. It's located 2.6 mi (4.1 km) from The Mac-Haydn Theatre. Other good choices within 5 miles include Chatham Travel Lodge and Mile Hill B&B.
What are some accommodations with pools in Chatham?
Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. The Yankee Inn and Berkshire Mountain Lodge are a couple of other choices with an onsite pool. View all hotels with pools in Chatham.
What is the best accommodation for staying close to Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What is staying in Chatham like?
Visitors can enjoy all that Chatham has to offer including the theaters and restaurants. This city also attracts tourists with its welcoming locals. In Chatham, there are 25 hotels and other accommodations to choose from. Find out more about Chatham.
What should I do while I'm visiting Chatham?
A favorite place to visit is The Mac-Haydn Theatre. You'll also find Kinderhook Lake and Queechy Lake in the area. Check out what more to see and do in Expedia's Chatham guide.
What's the seasonal weather like in Chatham?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.