Deals on vacations and trips to Chatham

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The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Save 100% on your flight
Price was $883, price is now $552 per person
$552
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,079, price is now $703 per person
$703
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
A 24-hour gym, free self parking, and laundry facilities are featured at this lodge. WiFi in public areas is free. A business center, a terrace, and a picnic area are also on offer.
Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
Price was $1,050, price is now $686 per person
$686
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $1,199, price is now $797 per person
$797
per person
Mar 4 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
The Manchester View

The Manchester View

2.5 out of 5
Save 100% on your flight
Price was $998, price is now $666 per person
$666
per person
Feb 4 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Top Chatham hotels deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $141 total per night
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Pool
Parking included
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$169 nightly
The price is $183 total per night
$183 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Free Cancellation
$79 nightly
The price is $90 total per night
$90 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $113 total per night
$113 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Free Cancellation
$88 nightly
The price is $99 total per night
$99 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$176 nightly
The price is $197 total per night
$197 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
This smoke-free hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
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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.

Popular places to visit

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.

The Mac-Haydn Theatre

Frequently asked questions

How much are vacation packages to Chatham?
Travelocity offers package deals to Chatham, as well as flights and hotels, starting from as low as $552. With the money you save, you could include some awesome tours or perhaps even tack on some extra days to your vacation.
Where can I get the best vacation package deals for Chatham?
Book your dream vacation with Travelocity. With access to 400 air carriers and a whopping 1,000,000 properties worldwide, selecting the perfect Chatham package deal couldn't be easier.
Why should I book my Chatham vacation package via Travelocity?
Whether you're on the hunt for the ultimate unplugged vacation or you crave the fun and excitement of a towering metropolis, booking everything with Travelocity saves you time, money and hassle. No need to search through hundreds of different websites for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7.
Can I save money on my Chatham car rental if I book it with a hotel or flight?
With a Chatham vacation package, you can combine your car, flight and hotel bookings and save a whole lot. If you want to uncover the best of this wonderful destination, why not make a beeline for Times Square? This renowned attraction is 110 mi from Chatham. With your own rental car, you'll be there in a jiffy.
Which airport is best for Chatham?
Many people arrive at Bradley Intl. Airport (BDL). After you've stepped off the plane and collected your bags, head 55 mi northwest to reach inner Chatham. Albany Intl. Airport (ALB) is your other choice, 30 mi from the center of the city.
What is there to do in Chatham?
The Mac-Haydn Theatre should be toward the top of your to-do list. After you've crossed off this famous attraction, simply wander the streets of Chatham and learn what really makes this fantastic place tick.
Where should I stay when visiting Chatham?
Many travelers choose to spend their nights at the BLUSH: Boutique TINY home w/ private spa. Walk to New York's cutest village.. It's a terrific base for your Chatham getaway.

Photos of local treasures

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