Chatham Holidays

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Top Flight + Hotel Deals in Chatham

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
per person
16 Oct - 20 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,658 reviews)
This is my 2nd time staying here. Good location to stay in Boston. Friendly & helpful staff. Room was clean and well maintained. Easily walkable to points of historical interest as the Freedom Trail is right up the street. We walked a lot (put in approx 20k+ steps a day) Great restaurants and bars in close proximity. Parking is in a garage a couple of blocks away that the hotel partners with for a discounted rate.

Reviewed on 23 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
9 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on 23 Jul 2025

Omni Parker House

Omni Parker House

4 out of 5
Downtown Boston
Save 100% on your flight
per person
16 Oct - 20 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.8/10 Excellent! (2,836 reviews)
The location of the property was perfect for our group to tour Boston on the four days that we stayed.

Reviewed on 23 Jul 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
per person
16 Oct - 20 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8/10 Very Good! (566 reviews)
Pros- Apartment itself is extremely spacious and clean/modern. Quiet, easy check in/check out process Cons- Probably won’t be able to hold your bags on the weekends prior to 4 which sucked. Fitness facilities out of order.

Reviewed on 4 Jul 2025

Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
per person
16 Oct - 20 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (1,087 reviews)
The staff not one time said hey how are you today or anything whenever we came in. It would be different if they had people at the desk but they weren’t. As we were leaving for the airport interesting of saying would you guys like someone to get your bags outside for you they watched us drag them down the stairs. I am also in a boot so it’s a little hard for me to walk so it would’ve been nice if I was asked if need help

Reviewed on 22 Jul 2025

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 €913 per night from 17 Aug to 18 Aug
€913
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (775 reviews)
"Old school hotel complex in a great location overlooking the Sea. Great ambience in the main lodge & dining facilities. Very kid friendly with the main pool swarming with kids. At one point I noticed 8 small kids in the large jacuzzi at one time - unusual for a luxury property. The pool experience ..."

Reviewed on 16 Jul 2025

Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
9.2/10 Wonderful! (526 reviews)
"Outdoor dinner staff stood around loudly talking the whole time we were seated at dinner."

Reviewed on 18 Jul 2025

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Chatham Wayside Inn
The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is €213 per night from 31 Jul to 1 Aug
€213
31 Jul - 1 Aug
includes taxes & fees
9.2/10 Wonderful! (614 reviews)
"Room was spacious and clean."

Reviewed on 10 Jul 2025

The Chatham Motel
See all 5,046 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

Monomoy National Wildlife Refuge

Explore the great outdoors at Monomoy National Wildlife Refuge, a lovely green space in Chatham. Amble around this trendy area's beautiful beaches and enjoy its seafood restaurants.

Monomoy National Wildlife Refuge

Atwood House Museum

You can spend an afternoon browsing the exhibits at Atwood House Museum in Chatham. Stroll along the seaside in this trendy area or visit its seafood restaurants.

Atwood House Museum

Frequently asked questions

How much does a Chatham holiday package cost?
Offering excellent value package deals from €1,062 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.