Deals on vacations and trips to Chatham

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Chatham flight + hotel vacation packages

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Jun 17 - Jun 20
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
A full-service spa, 2 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.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
per person
Jul 10 - Jul 17
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
This hotel features free WiFi in public areas, laundry facilities, and self parking. Enjoy the free buffet breakfast each morning. A computer station and luggage storage are also provided.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Jul 10 - Jul 17
Roundtrip flight included
Detroit (DTW) 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.
Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Save 100% on your flight
per person
Jul 10 - Jul 17
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
This aparthotel features free WiFi in public areas, luggage storage, and laundry facilities. Business travelers can take advantage of the 24-hour business center. Multilingual staff can provide around-the-clock assistance and concierge services are on offer.
Global Luxury Suites East Boston

Global Luxury Suites East Boston

4 out of 5
East Boston
Save 100% on your flight
per person
Jul 10 - Jul 17
Roundtrip flight included
Detroit (DTW) to Boston (BOS)
This aparthotel features an indoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. Enjoy the seasonal outdoor pool and perks like free WiFi.
Prices and availability subject to change. Additional terms may apply.

Top Chatham hotel deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is $445 per night
$445
per night
Apr 28 - Apr 29
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 a meal from the restaurant and perks like a free beach shuttle.
Chatham Wayside Inn

Chatham Wayside Inn

3.5 out of 5
512 Main St, Chatham, MA
The price is $186 per night
$186
per night
Apr 24 - Apr 25
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.
Chatham Seafarer Inn

Chatham Seafarer Inn

3.5 out of 5
2079 Main St, Chatham, MA
The price is $171 per night
$171
per night
Apr 24 - Apr 25
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
Free WiFi
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Free Cancellation
Reserve now, pay when you stay
The price is $120 per night
$120
per night
Apr 28 - Apr 29
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.
Cape Codder Resort and Spa

Cape Codder Resort and Spa

3 out of 5
1225 Iyannough Rd, Hyannis, MA
Free Cancellation
Reserve now, pay when you stay
The price is $107 per night
$107
per night
Apr 28 - Apr 29
This smoke-free resort features a full-service spa, a water park, and 2 restaurants. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the outdoor pool and perks like free self parking and free WiFi.
Hyannis Travel Inn

Hyannis Travel Inn

2.5 out of 5
18 North St, Hyannis, MA
Free Cancellation
Reserve now, pay when you stay
The price is $80 per night
$80
per night
Apr 28 - Apr 29
This hotel features an outdoor pool and an indoor pool. Enjoy the spa tub and free perks like continental breakfast and free self parking. Free WiFi in public areas, a terrace, and express check-out are also on offer.
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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

Image for Chatham Fish Pier

Chatham Fish Pier

4.5/5(8 reviews)

Explore the waterfront in Chatham with a trip to Chatham Fish Pier. Wander the beautiful beaches and seaside in the area.

Chatham Fish Pier
Image for Chatham Lighthouse

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 Lighthouse
Image for Chatham Windmill

Chatham Windmill

You can learn about the history of Chatham with a visit to Chatham Windmill. Stroll along the beautiful beaches in this trendy area, or check out its seafood restaurants.

Chatham Windmill

Frequently asked questions

How much are vacation packages to Chatham?
Splash out on a memorable experience in Chatham with a vacation package starting at $599. Locking in hotels, flights and tours with Travelocity is easy. And even better, our vacation deals will leave you with more savings for plenty of fun activities.
How long should my Chatham vacation be?
Around 2 nights is the average time frame travelers spend in Chatham. But the ideal trip length all depends on how many unforgettable memories you want to make. Why not allow a little more time and explore some of the lesser-known spots?
Where can I get the best vacation package deals for Chatham?
Landing an unbeatable package deal to Chatham is a piece of cake with Travelocity. With 400 airlines and 1,000,000 properties across the globe, you’ll have loads of choice when it comes to your flights and hotels.
Why should I purchase my Chatham vacation package via Travelocity?
By booking your flights, hotel, car rental and activities all in the one place, you’ll save big bucks as well as precious time. All our bookings come with an expert team of customer service specialists available 24/7, and you’ll know that you’ll always score the best deal possible with our Price Match Guarantee. So, what’s stopping you? Book the vacation of your dreams today and get packing!
Will I save money on my Chatham car rental if I combine it with my hotel or flight?
With a Chatham vacation package, you can bundle your car, hotel and flight bookings and save a whole lot. When you’re ready to discover the best of this impressive area, why not start with Fenway Park? This top attraction is 75 mi from Chatham. With your own wheels, you’ll be there before you know it.
What is the best time of year to go to Chatham?
If you’re watching your pennies, is a terrific month to visit, while is the costliest time of the year. April, May and June is the peak season. If you’d prefer to avoid the masses, October, November and December are usually quieter.
Which airport is best for Chatham?
Nantucket Memorial Airport (ACK) is one of the busiest airports in Chatham. It’s situated 30 mi south of the city center. Other choices include Martha’s Vineyard Airport (MVY) (40 mi away from central Chatham) and Barnstable Municipal Airport (HYA) (17 mi away from central Chatham).
What is there to do in Chatham?
Chatham has more than its fair share of places to discover, such as Chatham Lighthouse and Chatham Fish Pier. These well-known attractions top most travelers’ itineraries.
Where should I stay when visiting Chatham?
If you’re searching for a place to lay your head, take a look at the Chatham Wayside Inn. It’s the top pick for many visitors.