Chatham Holidays

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Chatham Holiday

Our pick of the best Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$1,607 per night from 17 Aug to 18 Aug
NZ$1,607
17 Aug - 18 Aug
includes taxes & 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 30 Jun. 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (521 reviews)
"to sit outside your view was the parking lot-ugh"

Reviewed on 13 Jul. 2025

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Chatham Wayside Inn
The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is NZ$421 per night from 21 July to 22 July
NZ$421
21 July - 22 July
includes taxes & fees
9.2/10 Wonderful! (614 reviews)
"Room was spacious and clean."

Reviewed on 10 Jul. 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.

Discover the most popular places to visit in Chatham

Monomoy National Wildlife Refuge

Explore the great outdoors at Monomoy National Wildlife Refuge, a lovely green space in Chatham. Amble around this trendy area's beautiful beaches and enjoy its seafood restaurants.

Monomoy National Wildlife Refuge

Veterans Field

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

Veterans Field

Caleb Nickerson House

You can spend an afternoon exploring the galleries in Caleb Nickerson House during your travels in Chatham. Amble around this family-friendly area's beautiful beaches and enjoy its seafood restaurants.

Caleb Nickerson House

What to do in Chatham

Chris and his brother enjoy a dark night at Nauset Light.

Private Guided Night Photography Tours on Cape Cod (for one photographer.)

NZ$708
per adult
Private Guided Night Photography Tours on Cape Cod (for one photographer.)
Private Professional Vacation Photoshoot in Cape Cod

Private Professional Vacation Photoshoot in Cape Cod

NZ$1,936
per adult
Private Professional Vacation Photoshoot in Cape Cod
See all activities in Chatham

Frequently asked questions

How much does a Chatham holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages. Choosing to travel in quieter periods means you'll typically find better prices on accommodation and flights.
How many days is enough for Chatham?
We'd recommend booking a Chatham holiday 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 neighbourhoods like South Chatham and South Harwich. You could even squeeze in one or two day trips beyond Chatham.
Is it worth booking a holiday package to Chatham?
Chatham has everything you need for a wonderful escape. Begin your Chatham holiday 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 holiday as a package?
An Expedia holiday 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 holiday 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 customised Chatham holiday package.

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