Chatham Vacation Packages 2025/2026 from $434

Chatham flight + hotel vacation packages

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

Boston Lodge and Suites

Dorchester

per person

Sep 20 - Sep 23

found 24 hours ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Six-Bedroom Family Retreat

per person

Sep 25 - Sep 30

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This guesthouse features a garden, laundry facilities, and free self parking. Dry cleaning and luggage storage are also provided.

Sea Mist Resort

Save 100% on your flight

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This aparthotel features an outdoor pool and an indoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.

The Colonnade Hotel Back Bay

Back Bay

Save 100% on your flight

per person

Oct 5 - Oct 10

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. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the seasonal outdoor pool, poolside bar, and laundry facilities.

Raffles Boston

Back Bay

Save 100% on your flight

per person

Oct 5 - Oct 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd, Chatham, MA

$940 nightly

$1,076 total

Aug 17 - Aug 18

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

$403 nightly

$461 total

Aug 24 - Aug 25

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 Chatham Motel

1487 Main Street, Chatham, MA

$219 nightly

$251 total

Jul 29 - Jul 30

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

The Hawthorne

196 Shore Rd, Chatham, MA

$435 nightly

$497 total

Jul 28 - Jul 29

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

Cape Sands Inn

149 Main St - RT 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$136 total

Aug 3 - Aug 4

Total includes taxes and fees

This motel features an indoor pool and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the picnic area. Enjoy the hot tub and perks like free self parking and free WiFi.

Pool

Hot Tub

Bayside Resort Hotel

225 Route 28, West Yarmouth, MA

Free Cancellation

Reserve now, pay when you stay

$235 nightly

$269 total

Aug 17 - Aug 18

Total includes taxes and fees

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

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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

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

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 $434. 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.