Chatham Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 AEDĀ 3,838 per night from Aug 12 to Aug 13
AEDĀ 3,838
AEDĀ 4,393 total
12 Aug - 13 Aug
includes taxes & fees
9.2/10 Wonderful! (845 reviews)
"Beautiful Cape Cod style Inn with every amenity you could want. Restaurants all had great menu selections"

Reviewed on 10 July 2026

Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
Fully refundableReserve now, pay when you stay
The price is AEDĀ 896 per night from Aug 5 to Aug 6
AEDĀ 896
AEDĀ 1,026 total
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (250 reviews)
"The property needed lots of updating. There was rotting wood, moldy showers and a lack of trash receptacles."

Reviewed on 17 July 2026

Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
The price is AEDĀ 1,823 per night from Jul 19 to Jul 20
AEDĀ 1,823
AEDĀ 2,246 total
19 Jul - 20 Jul
includes taxes & fees
Chatham Wayside Inn
See all 5,063 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.

Stay near popular Chatham attractions

A calm sea with several boats anchored near the shore.

Chatham Fish Pier

9.4/10 (107 reviews)
Watch local fishermen unload their daily catch while seals swim nearby at this authentic working waterfront. Savor fresh seafood from the on-site market while enjoying panoramic harbor views from the observation deck.
See properties

Frequently asked questions

How much does a Chatham vacation package cost?
You can grab a vacation package to this destination on Expedia. But how much your vacation to Chatham costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Chatham?
You're likely to find lower rates and greater availability in January, February and March. Explore our cheap Chatham vacation packages and you could land some great off-season discounts.
How to find the best Chatham package deals?
Use Expedia's filters to find some tempting Chatham package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chatham package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chatham vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Chatham trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Chatham?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Chatham trip.
How to plan a trip to Chatham?

  1. Choose your dates: The things you want to do in Chatham and your favorite season can help you decide when to go.
  2. Plan your budget wisely: On top of the price of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Chatham.
  3. Set the duration of your trip: Start by compiling a list of the activities and attractions you want to experience in Chatham. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the perfect Chatham vacation package for you.