Chatham Holidays

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Top Flight + Hotel Deals in Chatham

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel

The Revolution Hotel

South End
€675
per person
1 Dec - 6 Dec
found 15 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,891 reviews)
Boston Harbor Hotel

Boston Harbor Hotel

North End
€1,221
per person
1 Dec - 6 Dec
found 19 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Raffles Boston

Raffles Boston

Back Bay
€1,312
per person
1 Dec - 6 Dec
found 15 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (329 reviews)
Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

North Brookline
€1,075
per person
29 Oct - 4 Nov
found 16 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
7/10 Good! (6 reviews)
Great place, clean, well maintained and centrally located. Excellent and timely communication.

Reviewed on 25 Sept 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

Back Bay
€1,256
per person
28 Oct - 31 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,345 reviews)

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
€418
25 Oct - 26 Oct
includes taxes & fees
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

512 Main St Chatham MA
€309
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (738 reviews)
"Truthfully, I was underwhelmed. For almost $450 per night, I was expecting more. Our room was tiny. The first night, there was this constant drip outside our window that disturbed my husband’s sleep. He did tell the front desk the next morning and they did take care of it. No vending machine to grab ..."

Reviewed on 25 Sept 2026

Chatham Wayside Inn
Queen Anne Inn

Queen Anne Inn

70 Queen Anne Rd Chatham MA
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Queen Anne Inn
See all 4,987 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 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. Savour fresh seafood from the on-site market while enjoying panoramic harbour 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 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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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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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.
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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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Frequently asked questions

How much does a Chatham holiday package cost?
Offering excellent value package deals from €675 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.