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$20,852
NT$23,865 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (858 reviews)
"The food wasn’t great. It’s not like it looks in the pictures We stayed in the cottage. It really was not a difference to any room. The kids club was great. I don’t feel I need to go back"

Reviewed on 2026/8/21

Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
8.6/10 Excellent! (274 reviews)
"Property run down. Rm carpet disgusting No hot water 2 days Sink doesn’t drain No breakfast as advertised. Housekeeping done at 5:00 pm. Very inconvenient considering I was out of my room all day. Mgr very nice and understanding but used excuse that they’re remodeling soon over and over! However, ..."

Reviewed on 2026/8/23

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Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
NT$11,351
NT$14,377 total
Aug 25 - Aug 26
includes taxes & fees
9.2/10 Wonderful! (721 reviews)
"Great location, close to the famous Squire and the restaurant (Wild Goose Tavern) on-site was terrific and made the experience a positive one. Elena makes an awesome martini, and Bobby was a friendly welcoming personality. Ben was awesome during dinner. Hotel staff should take lessons from the restaurants ..."

Reviewed on 2026/8/17

Chatham Wayside Inn
See all 5,030 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 lighthouse with a glass enclosure and metal railing, set against a partly 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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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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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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Caleb Nickerson House

6.0/10 (1 review)
Step back in time at this preserved 1829 Cape-style house with three working fireplaces. Watch demonstrations of hearth cooking and colonial crafts while exploring the historic homestead's period rooms.
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Chatham Drama Guild

8.4/10 (6 reviews)
This intimate Cape Cod community theater showcases local talent through classic and contemporary productions. Reserve seats for an evening performance and experience authentic regional arts in a cozy, personal setting.
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Chatham Railroad Museum

8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chatham Railroad Museum during your travels in Chatham. Stroll along the area's beautiful beaches, or simply savor 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.