Chatham Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €185 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Chatham
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
North End
Price was €2,065, price is now €1,048 per person
€1,048
per person
18 Feb - 23 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Amazing, the gentleman who checked me in was world class! Room was spacious and immaculate. Thank you
Reviewed on 29 Dec 2025
Raffles Boston
Back Bay
Price was €1,667, price is now €1,231 per person
€1,231
per person
9 Feb - 13 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
Amazing week - family stay for Christmas in town - thank you very much! We’ll be back!…….
Reviewed on 28 Dec 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
297 Shore Rd Chatham MA
The price is €432 per night from 30 Dec to 31 Dec
€432
30 Dec - 31 Dec
includes taxes & fees
9.2/10 Wonderful! (798 reviews)
An incredible stay. Room at the main inn could use some updating. Just a bit tired with cracked tiles and some worn furniture, but overall the hotel is spectacular. The breakfast at Stars was amazing.
Reviewed on 14 Dec 2025
Chatham Wayside Inn
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (607 reviews)
Charming, cozy , clean!
Reviewed on 21 Dec 2025
Surfside Inn Chatham
25 Holway St Chatham MA
8/10 Very Good! (159 reviews)
This is a beautiful property very centrally located. I highly recommend the surfside inn.
Reviewed on 15 Oct 2025
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.
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.
What to do in Chatham
Private Professional Vacation Photoshoot in Cape Cod
€999
per adult
Explore a world of travel with Expedia
- 5 Star Hotels in Cape Cod
- Hotels near Bass River Sports World
- Historic Hotels in Brewster
- Brewster Hotels
- Aparthotels in Cape Cod
- Caravan Parks in Cape Cod
- Condo Rentals in Cape Cod
- Cottages in Cape Cod
- Guest Houses in Cape Cod
- Resorts in Cape Cod
- Adventure Sport Hotels in Cape Cod
- Beach Hotels in Cape Cod
- Bluegreen Resorts in Cape Cod
- Boutique Hotels in Cape Cod
- Golf Hotels in Cape Cod
- Hotels with Pool in Cape Cod
- Lgbt-Friendly Hotels in Cape Cod
- Luxury Hotels in Cape Cod
- Romantic Hotels in Cape Cod
- Wedding Hotels in Cape Cod
- Hotels near Cape Cod Inflatable Park
- Motels in Cape Cod
- Villas in Cape Cod
- Apartments in Chatham
- B&B in Chatham
- Beach Hotels in Chatham
- Chatham Hotels
- Hotels near Cranberry Valley Golf Course
- Dennis Hotels
- Cottages in Dennis Port
- Family Friendly Hotels in Dennis Port
- Dennis Port Hotels
- Eastham Hotels
- Harwich Hotels
- Beach Hotels in Harwich Port
- Hotels with Restaurant in Harwich Port
- Harwich Port Hotels
- Hotels near Mayflower Beach
- Hotels near Nauset Lighthouse
- North Chatham Hotels
- Orleans Hotels
- Hotels near Pirate's Cove Mini Golf
- Hotels near Rail Trail Bike Shop
- Hotels near Ridgevale Beach
- Hotels near Seagull Beach
- South Chatham Hotels
- South Yarmouth Hotels
- West Dennis Hotels
- West Harwich Hotels
- West Yarmouth Hotels
- Arnold's Mini Golf
- Atwood House Museum
- Bayberry Hills Golf Course
- Beach
- Bud's Go Karts
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Cape Cod National Seashore
- Visit Cape Cod
- Corn Hill Beach
- Craigville Beach
- Visit Dennis Port
- Englewood Beach
- Follins Pond
- Hyannis Holidays
- John F. Kennedy Hyannis Museum
- John F. Kennedy Memorial
- Monomoy National Wildlife Refuge
- Monomoy National Wildlife Refuge
- Nauset Beach
- Nauset Light Beach
- Ocean Edge Golf Club
- Paine's Creek Beach
- Visit Red Maple Swamp Trail
- Scargo Tower
- Seagull Beach
- Skaket Beach
- Visit South Dennis
- Visit South Yarmouth
- Twin Brooks Golf Course
- Wellfleet Harbor Actors Theater
- Wellfleet Holidays
- Werner Schmidt Observatory
- West Dennis Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
