Deals on vacations and trips to Chatham

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Chatham flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,340, price is now $529 per person
$529
per person
Jan 7 - Jan 11
found 23 hours ago
Roundtrip 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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,493, price is now $920 per person
$920
per person
Jan 15 - Jan 18
just found
Roundtrip flight included
Denver (DEN) 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.
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,122, price is now $2,211 per person
$2,211
per person
Dec 22 - Dec 28
found 1 hour ago
Roundtrip flight included
Denver (DEN) to Boston (BOS)
A full-service spa, 3 restaurants, and an indoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like free WiFi. You'll appreciate the a rooftop terrace, bar/lounge, and concierge services.
The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,072, price is now $778 per person
$778
per person
Jan 15 - Jan 18
just found
Roundtrip flight included
Denver (DEN) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Families will appreciate the onsite laundry facilities, kid-friendly dining, and babysitting. Enjoy the 24-hour gym and perks like free WiFi.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was $803, price is now $598 per person
$598
per person
Jan 15 - Jan 18
just found
Roundtrip flight included
Denver (DEN) to Boston (BOS)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. A computer station, dry cleaning, and luggage storage are also on offer.

Top Chatham hotels deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$361 nightly
The price is $413 total per night
$413 total
Nov 19 - Nov 20
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

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Free Cancellation
Reserve now, pay when you stay
$205 nightly
The price is $235 total per night
$235 total
Nov 22 - Nov 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
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28) Chatham MA
Get rates
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area and luggage storage are also provided.
Pool
Parking included
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
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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
The Hawthorne

The Hawthorne

2 out of 5
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
Old Harbor Inn

Old Harbor Inn

3.5 out of 5
22 Old Harbor Rd. Chatham MA
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A gym, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A coffee shop, a terrace, and a garden 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.

Stay near popular Chatham attractions

A beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)
If a restful vacation is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to seek out during your trip to Chatham. Stroll along this trendy area's seaside, or simply enjoy its seafood restaurants.
See properties

Frequently asked questions

How much are vacation packages to Chatham?
You can pick up a fantastic hotel and flight bundle for as low as $529. 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.

Photos of local treasures

Browse Chatham vacation photos for more inspiration

A lighthouse with a house nearby, under a starry night sky with visible Milky Way.
A lighthouse, a house, and a calm water body during sunset.
A lighthouse against a sunset sky.
A lighthouse with a red roof, white walls, and multiple flags, including the American flag, set against a sunset sky.
A coastal landscape with a prominent sandy peninsula surrounded by turquoise waters.

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