Chatham Vacations from $451

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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.
John Carver Inn & Spa

John Carver Inn & Spa

3 out of 5
Plymouth Cultural District
Save 100% on your flight
per person
Oct 4 - Oct 8
found 7 hours ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
8/10 Very Good! (1,003 reviews)
Great location.Walkable to many notable historic sites in town and awesome bars/restaurants. Clean, recently renovated & friendly staff. Fun pool for the kids and adults will enjoy the hot tub which could use some updates. The restaurant (CJs), was closed due to an emergency renovation. I was notified about a week prior to my arrival about the restaurant being closed. It didn’t really affect anything- there are many great places to eat. Overall, a good stay.

Reviewed on Jul 17, 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
per person
Sep 1 - Sep 6
found 10 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
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 28 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (775 reviews)
I like that they have fitness equipment in the room. Excellent

Reviewed on Jul 18, 2025

Fairfield Inn & Suites by Marriott Plymouth

Fairfield Inn & Suites by Marriott Plymouth

2.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
8.8/10 Excellent! (459 reviews)
Convenient, clean, great option away from the hustle of the waterfront

Reviewed on Jul 9, 2025

Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Save 100% on your flight
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
7.6/10 Good! (393 reviews)
Very nice area and big property offering many things. Only wish they had laundry services and also the toilet in our room was wobbly but it functioned.

Reviewed on Jul 18, 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
$835 nightly
The price is $955 total per night from Aug 17 to Aug 18
$955 total
Aug 17 - Aug 18
Total includes taxes and fees
9.2/10 Wonderful! (771 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
$484 nightly
The price is $554 total per night from Aug 18 to Aug 19
$554 total
Aug 18 - Aug 19
Total includes taxes and fees
9.2/10 Wonderful! (525 reviews)
"to sit outside your view was the parking lot-ugh"

Reviewed on Jul 13, 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 22 to Jul 23
$251 total
Jul 22 - Jul 23
Total includes taxes and fees
9.2/10 Wonderful! (614 reviews)
"Room was spacious and clean."

Reviewed on Jul 10, 2025

The Chatham Motel
See all 5,047 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 $451 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.