Chatham Vacation Packages 2025/2026 from $295

Chatham flight + hotel vacation packages

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

Even Hotels Manchester Airport by IHG

South End

Save 100% on your flight

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a snack bar/deli, and a lobby fireplace are also offered.

John Carver Inn & Spa

Plymouth Cultural District

Save 100% on your flight

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip flight included

Nashville (BNA) to Boston (BOS)

A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Motel 6 Danvers, MA - Boston North

Save 100% on your flight

per person

Oct 20 - Oct 27

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a snack bar/deli, and laundry facilities are also on offer.

The Revolution Hotel

South End

Save 100% on your flight

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a terrace are also on offer.

Ashworth by the Sea

Hampton Beach

Save 100% on your flight

per person

Oct 20 - Oct 27

found 21 hours ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

This smoke-free hotel features 3 restaurants, a bar/lounge, and an indoor pool. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$843 nightly

$965 total

Sep 7 - Sep 8

Total includes 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

$295 nightly

$338 total

Sep 1 - Sep 2

Total includes 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

The Hawthorne

196 Shore Rd, Chatham, MA

$303 nightly

$346 total

Sep 15 - Sep 16

Total includes taxes and fees

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

The Chatham Motel

1487 Main Street, Chatham, MA

$219 nightly

$251 total

Aug 25 - Aug 26

Total includes taxes and fees

A seasonal outdoor pool, free self parking, and free newspapers are featured at this motel. WiFi in public areas is free. A garden, a picnic area, and express check-in are also on offer.

Pool

Parking included

Margaritaville Resort Cape Cod

1225 Iyannough Rd, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$233 nightly

$267 total

Aug 24 - Aug 25

Total includes taxes and fees

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

Hyannis Plaza Hotel

662 Main Street, Hyannis, MA

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$117 total

Sep 17 - Sep 18

Total includes taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. There's a garden and multilingual staff can provide around-the-clock assistance.

Pool

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

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

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

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.

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 seaside 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 $295. 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.