Chatham Vacations

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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 3 kilometers 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 Hotel Deals

Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd Chatham MA
NT$12,467
NT$14,269 total
Nov 3 - Nov 4
includes taxes & fees
9.2/10 Wonderful! (870 reviews)
"Chatham Bars Inn is undoubtedly in a prime location and has all of the ingredients to be a great hotel. However, we stayed recently in the main building and the room (whilst ok) was very average, it looked tired and in need of a refurbishment - the bed in particular was disappointing and very uncomfortable ..."

Reviewed on 2026/10/8

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
NT$5,711
NT$7,923 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (746 reviews)
"Great 3 night stay at The Chatham Wayside. Right in the heart of the town on Main Street. Didn’t need a car for restaurants. Very impressed with the area , so clean. Highly recommend this Hotel"

Reviewed on 2026/10/7

Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

946 Main Street (Rte 28) Chatham MA
NT$5,122
NT$7,030 total
Nov 3 - Nov 4
includes taxes & fees
Greyfinch Chatham Inn
See all 4,959 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 vacation is part of your travel plans, Chatham Lighthouse Beach might be the perfect place to seek out during your trip to Chatham. Stroll along this trendy area's seaside, or simply enjoy its seafood restaurants.
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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 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.
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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 carefree 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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Cockle Cove Beach

9.0/10 (28 reviews)
If a restful vacation is part of your travel plans, Cockle Cove Beach might be the perfect place to seek out during your trip to 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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Mayo House

8.0/10 (3 reviews)
Learn about the local history of Chatham when you take a trip to Mayo House. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
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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.

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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.