Chatham Holidays

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Top Flight + Hotel Deals in Chatham

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was €819, price is now €692 per person
€692
per person
11 Dec - 13 Dec
just found
Return flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (1,636 reviews)

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was €1,387, price is now €920 per person
€920
per person
11 Dec - 13 Dec
just found
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
!

Reviewed on 10 Nov 2026

Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was €1,680, price is now €1,320 per person
€1,320
per person
11 Dec - 18 Dec
found 23 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,501 reviews)

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was €1,397, price is now €1,102 per person
€1,102
per person
11 Dec - 13 Dec
just found
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (343 reviews)

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was €940, price is now €810 per person
€810
per person
11 Dec - 13 Dec
just found
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,354 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

5 out of 5
297 Shore Rd Chatham MA
The price is €360 per night from 11 Nov to 12 Nov
€360
11 Nov - 12 Nov
includes taxes & fees
9.2/10 Wonderful! (876 reviews)
"Amazing place to stay. Can't wait to go back."

Reviewed on 30 Oct 2026

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
The price is €194 per night from 22 Nov to 23 Nov
€194
22 Nov - 23 Nov
includes taxes & fees
Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28) Chatham MA
8.8/10 Excellent! (302 reviews)
"………………………………………………………………."

Reviewed on 29 Oct 2026

Get rates
Greyfinch Chatham Inn
See all 4,699 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.
See properties

Frequently asked questions

How much does a Chatham holiday package cost?
Offering excellent value package deals from €692 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.