Chatham Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Chatham Beach Holiday

There's nothing that can beat a Chatham holiday. 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 travellers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town centre. However, you'll also find a fantastic range of Chatham holiday packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd Chatham MA
S$841
14 Sept - 15 Sept
includes taxes & fees
Chatham Bars Inn
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
8.6/10 Excellent! (273 reviews)
"The staff was very helpful for suggesting places to eat and visit"

Reviewed on 18 Aug, 2026

Get rates
Queen Anne Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
S$574
26 Aug - 27 Aug
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 17 Aug, 2026

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 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.
See properties
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.
See properties
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.
See properties

Chatham Drama Guild

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

Mayo House

8.0/10 (3 reviews)
Learn about the local history of Chatham with a stop at Mayo House. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.
See properties

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.
See properties

Chatham Railroad Museum

8.8/10 (3 reviews)
You can spend an afternoon browsing the exhibits at Chatham Railroad Museum in Chatham. Stroll along the area's beautiful beaches or simply savour its seafood restaurants.
See properties

Atwood House Museum

6.0/10 (1 review)
Step inside the 1752 Atwood House Museum to explore Cape Cod's maritime heritage through period antiques and local artefacts. Don't miss Alice Stallknecht's vibrant murals depicting 1930s Chatham life.
See properties

What to do in Chatham

Private Vacation Photoshoot with Photographer in Cape Cod

Private Vacation Photoshoot with Photographer in Cape Cod

S$407
per adult
Private Vacation Photoshoot with Photographer 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.