Chatham Vacation Packages 2026 from $1,104

Chatham flight + hotel vacation packages

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

Hutton Brickyards Riverfront Hotel + Venue

$1,104

per person

Dec 27 - Jan 2

found 12 hours ago

Roundtrip flight included

San Juan (SJU) 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.

Hotel Kinsley

Stockade District

Save 100% on your flight

$1,220

per person

Dec 27 - Jan 2

found 12 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.

Luxury Private Estate w Pool Near Rhinebeck

Save 100% on your flight

$9,710

per person

Dec 27 - Jan 2

found 12 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and barbecue grills are also provided.

Kingston Carriage House

Rondout

$1,232

per person

Dec 27 - Jan 2

found 12 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. A virtual front desk are provided for your convenience.

The Hideout Catskills Cottage

$1,282

per person

Dec 27 - Jan 2

found 12 hours ago

Roundtrip flight included

San Juan (SJU) to Albany (ALB)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden is also provided.

Top Chatham hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$108 nightly

$121 total

Nov 16 - Nov 17

Total with taxes and fees

This aparthotel 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

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

Free Cancellation

$101 nightly

$116 total

Nov 22 - Nov 23

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

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$119 total

Dec 16 - Dec 17

Total with taxes and fees

This aparthotel 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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

$192 nightly

$207 total

Dec 14 - Dec 15

Total with taxes and fees

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

Kitchen

Pet friendly

Comfort Inn Glenmont - Albany South

37 Route 9W Glenmont NY

Free Cancellation

$87 nightly

$100 total

Dec 6 - Dec 7

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 3 conference rooms, 24-hour business center, and laundry service. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$126 nightly

$141 total

Dec 12 - Dec 13

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

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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.

Stay near popular Chatham attractions

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.

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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 $1,104. 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.