Chatham Vacation Packages 2026 from $509

Chatham flight + hotel vacation packages

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

Hotel On North

$509

per person

Nov 5 - Nov 9

found 24 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking and luggage storage are also offered on site.

The Whitlock

$596

per person

Nov 5 - Nov 9

found 24 hours ago

Roundtrip flight included

Orlando (MCO) to Albany (ALB)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A business center, a terrace, and a garden are also on offer.

Brook Bound Inn

$1,142

per person

Dec 23 - Dec 27

found 15 hours ago

Roundtrip non-stop flight included

New York (JFK) to Albany (ALB)

A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.

The Cornell Inn, Lenox & The Berkshires

$841

per person

Nov 19 - Nov 23

found 12 hours ago

Roundtrip flight included

Philadelphia (PHL) to Albany (ALB)

A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

The Ponds at Foxhollow

$819

per person

Nov 19 - Nov 23

found 12 hours ago

Roundtrip flight included

Philadelphia (PHL) to Albany (ALB)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and conveniences like a terrace and laundry facilities.

Top Chatham hotels deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Nov 1 - Nov 2

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 1 - Nov 2

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

$111 nightly

$124 total

Nov 2 - Nov 3

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

$201 nightly

$217 total

Nov 2 - Nov 3

Total with taxes and fees

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

Kitchen

Pet friendly

The Yankee Inn

461 Pittsfield Rd Lenox MA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$118 total

Nov 1 - Nov 2

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

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$304 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free hotel features 3 indoor pools, a restaurant, and a bar/lounge. Enjoy the steam room and perks like free valet parking and free WiFi. Free self parking, a coffee shop, and a garden are also offered.

Pool

Spa

Don't see what you're looking for?

See all available properties in Chatham

View all properties

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.

See properties

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 $509. 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.