Chatham Holidays

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Chatham Holiday

Our pick of the best Chatham Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd Chatham MA
NZ$783
12 Nov - 13 Nov
includes taxes & fees
9.2/10 Wonderful! (873 reviews)
"Amazing property and staff."

Reviewed on 18 Oct 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
NZ$421
2 Nov - 3 Nov
includes taxes & fees
9.2/10 Wonderful! (755 reviews)
"Great location! Right in the heart of downtown Chatham. The restaurant was a bonus with standard Cape Cod cuisine and very yummy. They also provide bikes if you want to pedal around town. The breakfast included was a bit light, but there's a perfect Cafe next door. We'll definitely stay there ..."

Reviewed on 17 Oct 2026

Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

946 Main Street (Rte 28) Chatham MA
NZ$409
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (294 reviews)
"Clean room. Conveniently located. Friendly staff. Would say there again."

Reviewed on 16 Oct 2026

Greyfinch Chatham Inn
See all 4,916 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 beach with people walking and standing on the sand, and the ocean in the background.

Chatham Lighthouse Beach

9.2/10 (46 reviews)
If a restful holiday is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.
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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. Savour fresh seafood from the on-site market while enjoying panoramic harbour views from the observation deck.
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A lighthouse with an American flag, a white building with a red roof, and a cloudy sky.

Chatham Lighthouse

9.4/10 (173 reviews)
This historic 1808 beacon stands sentinel over Cape Cod's treacherous waters, guiding mariners for generations. Join a free summer Wednesday tour to climb the 48-foot tower for panoramic Atlantic views.
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A windmill, a boat, and a beach.

Chatham Windmill

9.2/10 (38 reviews)
This 1797 gristmill showcases Chatham's agricultural heritage with wooden gears and mechanisms. During summer "Corn Grinding Days," you can witness the historic mill transforming grain just as it did centuries ago.
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Ridgevale Beach

9.6/10 (21 reviews)
Why not spend a care-free afternoon at Ridgevale Beach during your travels in Chatham? Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.
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Chatham Seaside Links

9.2/10 (20 reviews)
This historic nine-hole course challenges golfers with coastal winds and strategic play along the Atlantic. Enjoy the natural undulations and ocean views while navigating the traditional seaside links layout.
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Cockle Cove Beach

9.0/10 (28 reviews)
If a restful holiday is part of your travel plans, Cockle Cove Beach might be the perfect place to visit during your trip to Chatham. Stroll along this trendy area's seaside or simply enjoy its seafood restaurants.
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Gallery Antonia

7.0/10 (2 reviews)
You can spend an afternoon browsing the exhibits at Gallery Antonia during your trip to Chatham. Stroll along the area's seaside or simply savour its seafood restaurants.
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What to do in Chatham

Private Vacation Photoshoot with Photographer in Cape Cod

Private Vacation Photoshoot with Photographer in Cape Cod

NZ$552
per adult
Private Vacation Photoshoot with Photographer in Cape Cod
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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.

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