Chatham Vacation Packages 2026 from $208

Chatham flight + hotel vacation packages

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

Vacation Village in the Berkshires

$208

per person

Apr 25 - Apr 27

found 1 day ago

Roundtrip flight included

Charlotte (CLT) 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.

The White House Inn

$653

per person

Apr 15 - Apr 19

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace and a garden are also provided.

The Springs Motel

$597

per person

Apr 15 - Apr 19

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this motel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.

Gregory House Country Inn

$566

per person

Apr 15 - Apr 19

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and a communal living room are also on offer.

Best Western Plus Berkshire Hills Inn & Suites

$225

per person

Apr 25 - Apr 27

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Top Chatham hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$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

$169 nightly

$183 total

Feb 8 - Feb 9

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 8 - Mar 9

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

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

190 Meadow Street South Lee MA

$130 nightly

$145 total

Feb 9 - Feb 10

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

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Free Cancellation

Reserve now, pay when you stay

$315 nightly

$355 total

Mar 8 - Mar 9

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop is provided and the front desk is staffed around-the-clock.

Free WiFi

Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

Free Cancellation

$102 nightly

$114 total

Mar 7 - Mar 8

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 $208. 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.