Deals on vacations and trips to Chatham

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Chatham flight + hotel vacation packages

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Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

2.5 out of 5
per person
Oct 1 - Oct 5
found 23 hours ago
Roundtrip flight included
New Orleans (MSY) to Albany (ALB)
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A computer station, luggage storage, and laundry facilities are also on offer.
The Wiltwyck

The Wiltwyck

3.5 out of 5
Save 100% on your flight
per person
Oct 1 - Oct 5
found 23 hours ago
Roundtrip flight included
New Orleans (MSY) 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
per person
Oct 1 - Oct 5
found 23 hours ago
Roundtrip flight included
New Orleans (MSY) 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
per person
Oct 1 - Oct 5
found 23 hours ago
Roundtrip flight included
New Orleans (MSY) 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.
Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Albany (ALB)
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free self parking, and a free airport shuttle. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. A computer station, dry cleaning, 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
$130 nightly
The price is $145 total per night
$145 total
Aug 27 - Aug 28
Total includes 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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Sep 7 - Sep 8
Total includes 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
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Aug 17 - Aug 18
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
Four Points by Sheraton Albany

Four Points by Sheraton Albany

3 out of 5
3 Mount Hope Way, Albany, NY
Free Cancellation
Reserve now, pay when you stay
$131 nightly
The price is $150 total per night
$150 total
Aug 24 - Aug 25
Total includes 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 24-hour gym and perks like free self parking.
Pool
Parking included
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Sep 1 - Sep 2
Total includes 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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $179 total per night
$179 total
Aug 17 - Aug 18
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
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 $373. 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