Chatham, NY

Travel Guide

A city street with buildings, parked cars, and solar panels.
A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
300 Broadway Albany NY
$110 nightly
The price is $126 total per night from Sep 29 to Sep 30
$126 total
Sep 29 - Sep 30
Total with taxes and fees
Book a stay at this business-friendly hotel in Albany. Enjoy free breakfast, free WiFi, and free parking. Popular attractions MVP Arena and Colonie Center Mall ...
8.2/10 Very Good! (1,092 reviews)
"Great rate, convenient location."

Reviewed on Sep 22, 2026

Country Inn & Suites by Radisson, Downtown Albany New York
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$122 nightly
The price is $136 total per night from Sep 23 to Sep 24
$136 total
Sep 23 - Sep 24
Total with taxes and fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,668 reviews)
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"

Reviewed on Sep 22, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundable
$108 nightly
The price is $120 total per night from Oct 22 to Oct 23
$120 total
Oct 22 - Oct 23
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,151 reviews)
"Clean room comfortABLE"

Reviewed on Sep 22, 2026

Berkshire Mountain Lodge
See all 1,629 properties in Chatham
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,668 reviews)
"I am disappointed that it has been over two weeks and I have yet to receive my room deposit back. They told me 7-10 days"

Reviewed on Sep 22, 2026

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,151 reviews)
"Clean room comfortABLE"

Reviewed on Sep 22, 2026

Berkshire Mountain Lodge
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all properties in Chatham
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.

Stay near popular Chatham attractions

The Mac-Haydn Theatre

You can enjoy a show at The Mac-Haydn Theatre on your trip to Chatham. Stroll along this trendy area's riverfront, or simply enjoy its coffeehouses.
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Frequently asked questions

Is Chatham worth visiting?
Chatham is worth visiting for its local dining, where travelers can enjoy Italian and North American cuisine. The destination also offers standout attractions like The Mac-Haydn Theatre, providing excellent entertainment and cultural experiences for visitors.
When is the best time to visit Chatham?
The best time to visit Chatham is from May through September, when the climate is most favorable for travelers. For fewer crowds and better value, the quieter months of December through March are a good option, offering a different experience with cooler temperatures.
What is Chatham known for?
Chatham is known as home to The Mac-Haydn Theatre, a performing arts venue that offers a range of productions. Travelers can also find a strong Italian food culture, with many dining options available.
What is a good itinerary length for Chatham?
A good itinerary length for Chatham is one day to experience The Mac-Haydn Theatre. For travelers looking to enjoy the local dining scene, including Italian, North American, and Asian cuisine, a two-day trip could be considered.
What are the top things to do in and around Chatham?
In Chatham, travelers can visit The Mac-Haydn Theatre, a local landmark.
What cuisines can you find in Chatham?
In Chatham you can find French cuisine, with dishes like coq au vin and boeuf bourguignon. Travelers can also enjoy Italian, North American, and fresh seafood options. For those seeking international flavors, there are also Asian choices such as Chinese and Japanese, as well as Mediterranean dishes.
Can I book a refundable hotel in Chatham?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Chatham by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Chatham with Expedia?
Expedia makes it easier to plan your Chatham trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Chatham?
The best choice depends on your travel style. Hotels in Chatham can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Chatham trip on Expedia?
Once you've booked your Chatham trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Chatham trip?
Expedia offers customer support before, during, and after your Chatham trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Chatham?
If it's your first trip to Chatham, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Chatham hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Chatham hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

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