Chatham Vacation Packages 2026 from $725

Chatham flight + hotel vacation packages

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

Hampton Inn Albany-Wolf Road (Airport)

$725

per person

May 3 - May 8

found 21 hours ago

Roundtrip flight included

Washington (DCA) 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.

Marriott Albany

$741

per person

May 3 - May 8

found 21 hours ago

Roundtrip flight included

Washington (DCA) to Albany (ALB)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and free airport shuttle. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Hilton Garden Inn Albany Airport

$810

per person

May 3 - May 8

found 21 hours ago

Roundtrip flight included

Washington (DCA) to Albany (ALB)

This hotel features an indoor pool, A 24-hour gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free airport shuttle. Unwind with a drink at the bar/lounge and enjoy perks like a free area shuttle.

Best Western Plus Franklin Square Inn Troy/Albany

$783

per person

May 3 - May 8

found 21 hours ago

Roundtrip flight included

Washington (DCA) to Albany (ALB)

A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. A business center, a coffee shop, and a terrace are also on offer.

Top Chatham hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

Feb 22 - Feb 23

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

282 Cairo Junction Rd Catskill NY

$150 nightly

$162 total

Feb 19 - Feb 20

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

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$136 total

Mar 15 - Mar 16

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

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Feb 22 - Feb 23

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

Quality Inn

372 Main Street Great Barrington MA

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$85 total

Feb 26 - Feb 27

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$150 total

Feb 18 - Feb 19

Total with 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.

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 $725. 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.