Deals on vacations and trips to Chatham

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Chatham flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $447, price is now $369 per person
$369
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Free WiFi in public areas is available at this guesthouse. Take advantage of the free self parking.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Save 100% on your flight
Price was $802, price is now $656 per person
$656
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Save 100% on your flight
Price was $655, price is now $540 per person
$540
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Kingston Carriage House

Kingston Carriage House

4 out of 5
Rondout
Price was $583, price is now $506 per person
$506
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.
The Hideout Catskills Cottage

The Hideout Catskills Cottage

2 out of 5
Save 100% on your flight
Price was $833, price is now $723 per person
$723
per person
Apr 3 - Apr 6
found 20 hours ago
Roundtrip flight included
Dallas (DFW) to Albany (ALB)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

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
$128 nightly
The price is $143 total per night
$143 total
Jan 28 - Jan 29
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
$159 nightly
The price is $172 total per night
$172 total
Jan 28 - Jan 29
Total with taxes and fees
This cabin features a virtual front desk. Take advantage of the free self parking.
Kitchen
Pet friendly
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $136 total per night
$136 total
Feb 26 - Feb 27
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W Glenmont NY
Free Cancellation
$84 nightly
The price is $96 total per night
$96 total
Feb 6 - Feb 7
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
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
$98 nightly
The price is $109 total per night
$109 total
Jan 30 - Jan 31
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
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Feb 10 - Feb 11
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
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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 $369. 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

Browse Chatham vacation photos for more inspiration

Tracy Memorial Village Hall, Chatham, New York
Tracy Memorial Village Hall, Chatham, New York

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