Chatham Vacation Packages 2026 from $660

Chatham flight + hotel vacation packages

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

Hotel Ivy Boston Common

Bay Village

Save 100% on your flight

$660

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

Free WiFi in public areas, luggage storage, and a safe deposit box are available at this hotel. There's locker space and multilingual staff can provide around-the-clock assistance.

Meco Hotel - Hostel

West End

Save 100% on your flight

$773

per person

Jul 20 - Jul 23

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A coffee shop, free WiFi in public areas, and a snack bar/deli are available at this hostel. Express check-in is also provided.

Nantucket Inn

$2,022

per person

Jul 22 - Jul 28

found 22 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

2 outdoor tennis courts, 2 hot tubs, and an indoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Enjoy a meal from the restaurant and perks like free self parking and a free beach shuttle.

By the Sea Guests Bed & Breakfast & Suites

$1,253

per person

Jul 22 - Jul 28

found 22 hours ago

Roundtrip non-stop flight included

Denver (DEN) to Boston (BOS)

This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Mandarin Oriental, Boston

Back Bay

Save 100% on your flight

$1,260

per person

Aug 13 - Aug 16

found 5 hours ago

Roundtrip flight included

Minneapolis (MSP) to Boston (BOS)

A full-service spa, a gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the sauna, bar/lounge, and limo/town car service.

Top Chatham hotels deals

Chatham Bars Inn

297 Shore Rd Chatham MA

$476 nightly

$545 total

May 20 - May 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

$294 nightly

$337 total

May 20 - May 21

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

Chatham Seafarer Inn

2079 Main St Chatham MA

$154 nightly

$176 total

Jun 3 - Jun 4

Total with taxes and fees

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

Queen Anne Inn

70 Queen Anne Rd Chatham MA

$261 nightly

$299 total

Jun 2 - Jun 3

Total with taxes and fees

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

Captain's House Inn

369 Old Harbor Road Chatham MA

Get rates

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

Margaritaville Resort Cape Cod

1225 Iyannough Rd Hyannis MA

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$251 total

May 20 - May 21

Total with 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

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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.

Chatham Fish Pier

4.5/5(10 reviews)

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.

Historic Wind Mill at Chatham, Cape Cod Harbor

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 $660. 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.