Chatham Vacation Packages 2026 from $636

Chatham flight + hotel vacation packages

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

Hotel Brookmere & Arbor Spa

$636

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Lodges At Cresthaven

$835

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

Bluebird Spa City Motor Lodge

Downtown Saratoga Springs

$662

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Albany (ALB)

This hotel features free WiFi in public areas, concierge services, and self parking. Express check-out and luggage storage are also provided.

Ambler Hotel

$675

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-out is also provided.

Sundowner on Lake George

$770

per person

May 20 - May 23

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Albany (ALB)

A private beach and a hot tub are featured at this smoke-free motel. Enjoy the seasonal outdoor pool and perks like free self parking. A terrace, a picnic area, and laundry facilities are also on offer.

Top Chatham hotels deals

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

$159 nightly

$172 total

Mar 25 - Mar 26

Total with taxes and fees

This cabin features a virtual front desk. Take advantage of the free self parking.

Kitchen

Pet friendly

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

Free Cancellation

$114 nightly

$131 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. 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.

Breakfast included

Parking included

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$120 total

Apr 22 - Apr 23

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

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$78 nightly

$87 total

Mar 29 - Mar 30

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.

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

190 Meadow Street South Lee MA

Free Cancellation

$130 nightly

$145 total

Mar 28 - Mar 29

Total with taxes and fees

This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.

Pool

Air conditioning

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$123 nightly

$137 total

Mar 26 - Mar 27

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

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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 $636. 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.