Chatham Vacation Packages 2026 from $361

Chatham flight + hotel vacation packages

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

The Wylie Inn and Conference Center at Endicott College

$361

per person

Feb 25 - Mar 1

found 1 day ago

Roundtrip flight included

Denver (DEN) to Boston (BOS)

A 24-hour gym, free self parking, and wedding services are featured at this hotel. WiFi in public areas is free. A coffee shop, a computer station, and luggage storage are also on offer.

By the Sea Guests Bed & Breakfast & Suites

Save 100% on your flight

$623

per person

Mar 3 - Mar 7

found 2 hours ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Boston Harbor Hotel

North End

$1,354

per person

Mar 5 - Mar 8

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

A marina, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the indoor pool and perks like free WiFi.

The Coach House

$943

per person

Mar 13 - Mar 20

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Boston (BOS)

This hotel features free self parking and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.

DoubleTree by Hilton Manchester Downtown

Downtown Manchester

$828

per person

Apr 3 - Apr 10

found 20 hours ago

Roundtrip non-stop flight included

Los Angeles (LAX) to Boston (BOS)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Self parking, a business center, and a coffee shop are also offered.

Top Chatham hotels deals

Chatham Wayside Inn

512 Main St Chatham MA

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$179 total

Jan 22 - Jan 23

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 Bars Inn

297 Shore Rd Chatham MA

$364 nightly

$417 total

Jan 22 - Jan 23

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

Surfside Inn Chatham

25 Holway St Chatham MA

Get rates

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

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

Chatham MA

Get rates

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

The Hawthorne

196 Shore Rd Chatham MA

Get rates

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

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

Don't see what you're looking for?

See all available properties in Chatham

View all properties

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.

Cape Cod hidden treasure...sunrise in Chatham

Monomoy National Wildlife Refuge

4.5/5(2 reviews)

Explore the great outdoors at Monomoy National Wildlife Refuge, a lovely green space in Chatham. Amble around this trendy area's beautiful beaches and enjoy its seafood restaurants.

Chatham Fish Pier

4.5/5(8 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.

Frequently asked questions

How much are vacation packages to Chatham?

You can pick up a fantastic hotel and flight bundle for as low as $361. 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.