Chatham Vacation Packages 2025 from $357

Chatham flight + hotel vacation packages

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

The Beverly

per person

Mar 1 - Mar 5

found 20 hours ago

Roundtrip non-stop flight included

Orlando (MCO) to Boston (BOS)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-in. Express check-out and a virtual front desk are also provided.

Fairmont Copley Plaza, Boston

Back Bay

per person

Mar 7 - Mar 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a rooftop terrace on site, and laundry facilities and concierge services are also offered.

Raffles Boston

Back Bay

Save 100% on your flight

per person

Feb 6 - Feb 9

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A full-service spa, 3 restaurants, and an indoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and rooftop terrace.

Hampton Inn Boston Logan Airport Chelsea

Save 100% on your flight

per person

Jan 29 - Feb 3

found 1 day ago

Roundtrip flight included

Miami (MIA) to Boston (BOS)

A 24-hour gym, self parking, and laundry facilities are featured at this hotel. Guests will appreciate freebies like continental breakfast, WiFi in public areas, and a roundtrip airport shuttle. A picnic area and luggage storage are also provided.

Upscaled Home in a Quiet Neighborhood

Forest Park

Save 100% on your flight

per person

Feb 24 - Mar 2

found 21 hours ago

Roundtrip flight included

San Juan (SJU) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$409

includes taxes & fees

$357 per night

Jan 15 - Jan 16, 2025

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

$233

includes taxes & fees

$204 per night

Jan 1 - Jan 2, 2025

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

Chatham Seafarer Inn

2079 Main St, Chatham, MA

Get rates

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

Pool

Parking included

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$134

includes taxes & fees

$117 per night

Jan 5 - Jan 6, 2025

This hotel features 2 poolside bars, 2 bars/lounges, and an indoor pool. Enjoy the gym and free perks like buffet breakfast and free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Hot Tub

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

867 Iyannough Road, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$106

includes taxes & fees

$93 per night

Jan 12 - Jan 13, 2025

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free Cancellation

$178

includes taxes & fees

$155 per night

Jan 8 - Jan 9, 2025

This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a lazy river and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.

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.

Popular places to visit

Chatham Lighthouse

4.5/5(31 reviews)

Learn about the local history of Chatham when you spend time at Chatham Lighthouse. Wander the beautiful beaches and seaside in this trendy area.

Enjoy the view, watch the fishing boats come in and unload their catch, and pick up fresh fish or seafood to take home for dinner at the market.

Chatham Fish Pier

4.5/5(8 reviews)

Explore the waterfront in Chatham with a trip to Chatham Fish Pier. Wander the beautiful beaches and seaside in the area.

This windmill, The Godfrey Windmill, in Chase Park has none of its sheets mounted to the vanes. The expression "three sheets to the wind" originated because a windmill with only three sheets deployed will not

Chatham Windmill

You can learn about the history of Chatham with a visit to Chatham Windmill. Stroll along the beautiful beaches in this trendy area, or check out its seafood restaurants.

Frequently asked questions

How much are vacation packages to Chatham?

You can pick up a fantastic hotel and flight bundle for as low as $357. 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.