Chatham Vacation Packages 2026 from $507

Chatham flight + hotel vacation packages

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

Vacation Village in the Berkshires

$507

per person

Aug 5 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

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.

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Save 100% on your flight

$2,284

per person

Sep 3 - Sep 8

found 10 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Albany (ALB)

This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

$1,080

per person

Sep 3 - Sep 8

found 10 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Berkshire Mountain Lodge

$511

per person

Aug 5 - Aug 7

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

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.

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

$843

per person

Aug 20 - Aug 23

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Chatham hotels deals

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

Free Cancellation

$103 nightly

$117 total

Jul 12 - Jul 13

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center, conference center, and conference space. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Breakfast included

Parking included

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$143 nightly

$159 total

Jul 6 - Jul 7

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

The Yankee Inn

461 Pittsfield Rd Lenox MA

$159 nightly

$178 total

Jul 6 - Jul 7

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$162 nightly

$181 total

Jul 30 - Jul 31

Total with taxes and fees

Pool

Hot Tub

The Red Lion Inn

30 Main Street Stockbridge MA

$192 nightly

$214 total

Jul 20 - Jul 21

Total with taxes and fees

This historic 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. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Spa

Berkshires Untold

194 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$183 nightly

$205 total

Jul 6 - Jul 7

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 $507. 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.