Chatham Vacation Packages 2026 from $517

Chatham flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

$517

per person

Feb 8 - Feb 12

found 1 hour ago

Roundtrip non-stop flight included

Tampa (TPA) to Boston (BOS)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Families will appreciate the playground, onsite laundry facilities, and in-room childcare. A hair salon, a picnic area, and express check-out are also on offer.

The McKernan Inn

$603

per person

Mar 29 - Apr 2

found 20 hours ago

Roundtrip non-stop flight included

Richmond (RIC) to Boston (BOS)

This inn features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A garden, a picnic area, and luggage storage are also on offer.

Hyatt Regency Boston Harbor

East Boston

Save 100% on your flight

$819

per person

Mar 13 - Mar 17

found 12 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate perks like free WiFi and a free airport shuttle. Valet parking, a 24-hour business center, and a terrace are also offered.

Boston Marriott Cambridge

MIT

$681

per person

Mar 13 - Mar 17

found 12 hours ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A garden, express check-out, and a computer station are also on offer.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd Chatham MA

$488 nightly

$559 total

Jan 7 - Jan 8

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

Free Cancellation

Reserve now, pay when you stay

$172 nightly

$197 total

Jan 19 - Jan 20

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

Surfside Inn Chatham

25 Holway St Chatham MA

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This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a lobby fireplace, and express check-in are also on offer.

Breakfast included

Parking included

The Hawthorne

196 Shore Rd Chatham MA

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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

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham MA

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This vacation home features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.

Pool

Hot Tub

Captain's House Inn

369 Old Harbor Road Chatham MA

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This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.

Breakfast included

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.

Popular places to visit

Chatham Lighthouse

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

After visiting Chatham Fish Pier, make a plan to see the other sights and activities in Chatham. 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

Chatham Windmill is just one of the places to see in Chatham, so why not enjoy the other things to explore during your travels? 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 $517. 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.