Chatham Vacations from $343

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Your Chatham Vacation

Spend less time travel planning and more time having thrilling adventures with a Chatham vacation package. The neighborhood of Harwich Center, which is great for golfing and festivals, makes a great base for your city escape. If your trip to Chatham includes some sightseeing, take in renowned attractions like Chatham Lighthouse Beach, Bank Street Beach and Chatham Lighthouse. Check out Expedia's extensive range of travel options and begin planning your ultimate vacation to Chatham now.

The Latest Chatham vacation packages

Price found within the past 48 hours. Click for updated prices.
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
South End
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (748 reviews)
employees very friendly.

Reviewed on Jul 11, 2025

Ocean Air Suites

Ocean Air Suites

2.5 out of 5
Hampton Beach
Save 100% on your flight
per person
Sep 24 - Sep 28
found 20 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
9.2/10 Wonderful! (32 reviews)
location was awesome. able to see fireworks right from deck in the back. It’s definitely family friendly would definitely be coming back again next year :)

Reviewed on Sep 3, 2024

Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Boston (BOS)
7.8/10 Good! (715 reviews)
It’s my favorite place to go check list

Reviewed on Jul 10, 2025

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (576 reviews)
Very clean. The room is decorated in a very stylish manner that goes with the theme of the city. Located conveniently within walking distance to the city center.

Reviewed on Jul 11, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Best hotel I've stayed in. Only con would be sofa mattress. Other than that it was excellent.

Reviewed on Jul 10, 2025

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Discover the most popular places to visit in Chatham

Chatham Lighthouse

Chatham Lighthouse

4.5/5(31 reviews)

One of the most photographed of Cape Cod’s historic lighthouses overlooks a beautiful, white sand beach that’s great for fun in the sun.

Chatham Lighthouse
Enjoy the view, watch the fishing boats come in and unload their catch, and pick up fresh fish or seafood to take home for dinner at the market.

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
This windmill, The Godfrey Windmill, in Chase Park has none of its sheets mounted to the vanes. The expression "three sheets to the wind" originated because a windmill with only three sheets deployed will not

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 beautiful beaches in this trendy area, or check out its seafood restaurants.

Chatham Windmill

Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
$1,138 nightly
The price is $1,302 total per night from Jul 13 to Jul 14
$1,302 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (769 reviews)
"Absolutely gorgeous property. Everything was top notch and close enough to be able to walk into town. Just what we were looking for."

Reviewed on Jun 30, 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
$529 nightly
The price is $606 total per night from Jul 28 to Jul 29
$606 total
Jul 28 - Jul 29
Total includes taxes and fees
9.2/10 Wonderful! (515 reviews)
"Great hotel"

Reviewed on Jul 5, 2025

Chatham Wayside Inn
The Chatham Motel
The Chatham Motel
2 out of 5
1487 Main Street, Chatham, MA
$219 nightly
The price is $251 total per night from Jul 14 to Jul 15
$251 total
Jul 14 - Jul 15
Total includes taxes and fees
9.2/10 Wonderful! (611 reviews)
"The staff was so polite and accommodating! Jennifer is the best! The room was immaculate and it looks like it was recently renovated. Convenient to shopping and beaches. Would highly recommend it! Will be back again soon."

Reviewed on Jul 6, 2025

The Chatham Motel
See all 5,045 properties in Chatham
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.

Find the Best Chatham Vacation Packages

Chatham Beach Vacation

There's nothing that can beat a Chatham vacation. Whether you're indulging in fancy cocktails at a local hot spot or flipping through a book by the shore, your trip to Chatham is the perfect time to live out your beachy dreams. Many travelers will tell you to stay near Ridgevale Beach, located just 2 miles (4 km) from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Chatham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Nantucket Memorial Airport (ACK)
Population
1,400
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Nauset Beach, West Dennis Beach and Skaket Beach

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Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals from $343 on Expedia, you'll be pleasantly surprised at how much a vacation to Chatham costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chatham?
October, November and December are the best times to look for cheap Chatham vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Chatham?
Chatham vacations can be short or long, but to get a real feel for this destination, we reckon 3 days is a good ballpark. This will mean you can fit in top sights like Chatham Fish Pier and Chatham Lighthouse and seek out some hidden gems. Don't forget to explore cool neighborhoods such as Harwich Center and South Harwich either. If you're smart with your time, you may even be able to take a day trip or two from Chatham too.
Is it worth booking a vacation package to Chatham?
It's easy to see why a Chatham vacation is on the must-do list of many travelers. Major attractions like Chatham Fish Pier are just the start of things to keep you busy here.
How to find the best Chatham package deals?
Start your search for a Chatham package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Chatham package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chatham escape underway.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and stays individually. Better still, you can tailor your Chatham trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Chatham?
If you're planning a spur-of-the-moment Chatham adventure, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Chatham?

  1. Pick your dates: The things you'd like to do in Chatham and your favorite season will help you decide when to go.
  2. Plan your budget wisely: As well as the price of your stay, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may come up during your trip to Chatham.
  3. Explore Chatham using Expedia's trip planning tool: Gain insights into the top attractions and best properties for your trip to Chatham. You can also save your must-visit places, collaborate with your group and manage your plans in one place.
  4. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Chatham. Then, estimate how long you'll need at each, along with any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Chatham vacation package.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the best Chatham has to offer. Find all the exciting things to do in Chatham with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Chatham vacation packages?
Your Chatham break should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.