Chatham Holidays

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Top hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is 13.975.062 ₫ per night from 22 Sept to 23 Sept
13.975.062 ₫
16.794.181 ₫ total
22 Sept - 23 Sept
includes taxes & fees
9.2/10 Wonderful! (782 reviews)
"5 star experience!!"

Reviewed on 4 Aug 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (538 reviews)
"Great hotel in perfect location. Easy parking and right in the Main Street. Lovely bar in hotel. Restaurant food good - service a little poor at restaurant. Breakfast choice not great….but overall a great stay and would recommend."

Reviewed on 17 Aug 2025

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Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
8.8/10 Excellent! (235 reviews)
Greyfinch
"It was very nice. Property is clean, quiet, nice pool, close to main street, market, restaurants in walking distance. Rooms are very nice."

Reviewed on 25 Jul 2025

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Greyfinch Chatham Inn
See all 5,031 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.

Popular places to visit

Chatham Fish Pier

Chatham Fish Pier

Explore the waterfront in Chatham with a trip to Chatham Fish Pier. Wander the beautiful beaches and seaside in the area.

Chatham Fish Pier
Chatham Lighthouse

Chatham Lighthouse

Learn about the local history of Chatham when you take a trip to Chatham Lighthouse. Wander through the beautiful beaches and seaside in this trendy area.

Chatham Lighthouse
Chatham Windmill

Chatham Windmill

Chatham Windmill is just one of the places to see in Chatham, so why not enjoy the other things to explore during your travels? Stroll along the seaside in this trendy area or visit its seafood restaurants.

Chatham Windmill

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.