Chatham Vacation Packages 2026 from $431

Chatham flight + hotel vacation packages

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

Battery Wharf Hotel, Boston Waterfront

North End

$431

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a sauna on site, and laundry facilities and concierge services are also offered.

Boston Harbor Hotel

North End

$678

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,189

per person

Nov 4 - Nov 7

found 1 day ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

The Cove at Yarmouth by Westgate Resorts

Save 100% on your flight

$1,199

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Austin (AUS) to Boston (BOS)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. 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.

Iris Hotel Boston

Coolidge Corner

Save 100% on your flight

$1,447

per person

Oct 20 - Oct 27

found 9 hours ago

Roundtrip flight included

Austin (AUS) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd Chatham MA

$561 nightly

$642 total

Sep 20 - Sep 21

Total with taxes and fees

A private beach, a full-service spa, and 3 outdoor tennis courts are all featured at this luxury resort. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the gym and perks like free valet parking and a free beach shuttle.

On private beach

Pool

Chatham Wayside Inn

512 Main St Chatham MA

$397 nightly

$454 total

Sep 29 - Sep 30

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Enjoy the seasonal outdoor pool and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Pool

Breakfast included

Pleasant Bay Village Resort

1191 Orleans Road Chatham MA

$213 nightly

$243 total

Sep 22 - Sep 23

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, luggage storage, and laundry facilities are also on offer.

Pool

Hot Tub

Queen Anne Inn

70 Queen Anne Rd Chatham MA

Get rates

This hotel features a gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a lobby fireplace, and a library are also on offer.

Pool

Parking included

Greyfinch Chatham Inn

946 Main Street (Rte 28) Chatham MA

$210 nightly

$240 total

Oct 1 - Oct 2

Total with taxes and fees

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area and luggage storage are also provided.

Pool

Parking included

The Hawthorne

196 Shore Rd Chatham MA

Get rates

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.

On private beach

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.

Stay near popular Chatham attractions

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)

If a restful vacation is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to seek out during your trip to Chatham. Stroll along this trendy area's seaside, or simply enjoy its seafood restaurants.

See properties

Frequently asked questions

How much are vacation packages to Chatham?

You can pick up a fantastic hotel and flight bundle for as low as $431. With a Travelocity vacation package, a trip to Chatham has never looked more enticing! Save both time and money and then get a start on packing those bags.

How long should my Chatham vacation be?

There are no rules for how long your Chatham vacation should be, but many travelers decide to stay around 3 nights. Got some wiggle room in your departure date? Consider booking a few more nights. Then you'll have enough time to check out the area's hidden treasures as well.

Where can I get the best vacation package deals for Chatham?

It's simple — browse Travelocity. With no less than 400 airlines and 1,000,000 properties worldwide, it's a piece of cake to craft a Chatham package deal that suits your travel style.

Why should I purchase my Chatham vacation package via Travelocity?

We have destinations and experiences for every type of globetrotter, top-quality service and 24/7 support. In addition to that, we'll match any better price you happen to find with our Price Match Guarantee.

Will I save money on my Chatham car rental if I combine it with hotels and flights?

You sure can — combine your hotel, car and flight into a Chatham vacation package and you can save a tidy sum. With so many things to do in and around Chatham, that set of wheels will make exploring a joy. Once you're behind the wheel, get out on the wide open road and make tracks to Fenway Park, an unmissable sight approximately 75 mi from Chatham.

Which airport is best for Chatham?

Martha's Vineyard Airport (MVY) is a major hub. You'll find it approximately 40 mi southwest of Chatham. Your other options are Nantucket Memorial Airport (ACK) (30 mi away from central Chatham) and Provincetown Municipal Airport (PVC) (30 mi away from central Chatham).

What is there to do in Chatham?

While taking the path less traveled is rewarding, you shouldn't ignore the big-name attractions that make a destination famous. Monomoy National Wildlife Refuge and Veterans Field are a couple of them in Chatham.

Where should I stay when visiting Chatham?

If you're after a place to base yourself, check out the Chatham Wayside Inn. It's the top choice for many travelers.