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 $1,425, price is now $576 per person
$576
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $2,036, price is now $1,152 per person
$1,152
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,527, price is now $1,511 per person
$1,511
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Save 100% on your flight
Price was $1,446, price is now $915 per person
$915
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
This apartment features a virtual front desk. Take advantage of the self parking.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Save 100% on your flight
Price was $1,017, price is now $665 per person
$665
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Top Chatham hotels deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
$1,045 nightly
The price is $1,196 total per night
$1,196 total
Jul 29 - Jul 30
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
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
Free Cancellation
Reserve now, pay when you stay
$256 nightly
The price is $292 total per night
$292 total
Aug 18 - Aug 19
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
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
$534 nightly
The price is $611 total per night
$611 total
Aug 16 - Aug 17
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
Pleasant Bay Village Resort

Pleasant Bay Village Resort

3 out of 5
1191 Orleans Road Chatham MA
$299 nightly
The price is $342 total per night
$342 total
Aug 12 - Aug 13
Total with taxes and fees
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, luggage storage, and laundry facilities are also on offer.
Pool
Hot Tub
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28) Chatham MA
$391 nightly
The price is $448 total per night
$448 total
Aug 23 - Aug 24
Total with taxes and fees
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
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd Hyannis MA
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $312 total per night
$312 total
Aug 19 - Aug 20
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. Relax with a drink at one of the 2 poolside bars and enjoy free perks like free self parking and WiFi in public areas.
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.

Stay near popular Chatham attractions

A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 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.
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Frequently asked questions

How much are vacation packages to Chatham?
You can pick up a fantastic hotel and flight bundle for as low as $576. 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 boat on a calm river, a large house with a red roof, and dense greenery in the background.
A windmill by the sea with a clear sky.
A beach with houses in the background and people standing on the shore.
A calm lake with several boats anchored, surrounded by lush green trees and a large house in the background.
A lighthouse with an American flag and a smaller flag with a blue eagle.

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