Chatham Vacations

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Find the Best Chatham Vacation Packages

Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is ₩1,062,388 per night from Jul 23 to Jul 24
₩1,062,388
₩1,276,698 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (768 reviews)
"Excellent!"

Reviewed on Jun 24, 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (508 reviews)
"Great stay. Our dinner order was misplaced and we waited while others who arrived after us were eating their main course"

Reviewed on Jun 20, 2025

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Chatham Wayside Inn
Greyfinch Chatham Inn
Greyfinch Chatham Inn
3 out of 5
946 Main Street (Rte 28), Chatham, MA
8.8/10 Excellent! (221 reviews)
"Excellent property! It was very clean, the pool fire pit area was very nice and well maintained. Staff was friendly and helpful too! I will definitely stay again."

Reviewed on Jun 23, 2025

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Greyfinch Chatham Inn
See all 5,072 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.

Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals 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?
January, February and March are great times to search for cheap Chatham vacation packages. Choosing to travel in quieter periods means you'll typically find better prices on accommodations and flights.
How many days is enough for Chatham?
We'd recommend booking a Chatham vacation for a minimum of 3 days. This gives you time to tick off top attractions including Chatham Drama Guild and Monomoy National Wildlife Refuge, and also explore neighborhoods like South Chatham and South Harwich. You could even squeeze in one or two day trips beyond Chatham.
Is it worth booking a vacation package to Chatham?
Chatham has everything you need for a wonderful escape. Begin your Chatham vacation on a high note by checking out top attractions like Ridgevale Beach.
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 the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chatham.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the largest expense during your trip to Chatham.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Chatham. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Chatham vacation package.

Discover the most popular places to visit in Chatham

Veterans Field

Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Veterans Field
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.