Chatham Vacation Packages

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Your Chatham Vacation

Spend less time travel planning and more time having thrilling adventures with a Chatham vacation package. The neighborhood of Harwich Center, which is great for golfing and festivals, makes a great base for your city escape. If your trip to Chatham includes some sightseeing, take in renowned attractions like Chatham Lighthouse Beach, Bank Street Beach and Chatham Lighthouse. Check out Expedia's extensive range of travel options and begin planning your ultimate vacation to Chatham now.

Top Chatham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sea Mist Resort

Sea Mist Resort

3 out of 5
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.8/10 Excellent! (115 reviews)
we had a great stay with our grandchildren

Reviewed on Feb. 17, 2025

The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
Save 100% on your flight
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
Property was lovely. Enjoyed how quiet it was. Beach close by shuttle service very convenient. Everyone was friendly. Room was clean. Would stay here again.

Reviewed on Mar. 16, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
per person
Jun. 9 - Jun. 12
found 6 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
I felt very safe as a solo female traveler, anything you could ever want they can make available for you with a list of extra amenities that can be requested. Staff were kind and professional with good recommendations. I could easily walk to most things- The Harbor for my harbor cruise and north end for my tour I did out there. Overall very good stay, will stay again.

Reviewed on Mar. 18, 2025

Riverview Resort

Riverview Resort

3 out of 5
Bass River
Save 100% on your flight
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.2/10 Wonderful! (156 reviews)
I'll definitely be back!!!

Reviewed on Oct. 30, 2024

The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
per person
Jun. 9 - Jun. 12
found 6 hours ago
Roundtrip flight included
Buffalo (BUF) to Boston (BOS)
9/10 Wonderful! (1,805 reviews)
Clean, convenient, cordial staff

Reviewed on Mar. 25, 2025

Chatham Beach Vacation

There's nothing that can beat a Chatham vacation. 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 travelers will tell you to stay near Ridgevale Beach, located just 3 kilometres from the town center. However, you'll also find a fantastic range of Chatham vacation packages close to Hardings Beach and Cockle Cove Beach, two other well-loved nearby options.

Ready to book your vacation to Chatham?

 

Choose your dates

Chatham Hotel Deals

Chatham Bars Inn
Chatham Bars Inn
5 out of 5
297 Shore Rd, Chatham, MA
The price is CA $487 per night from Mar. 30 to Mar. 31
CA $487
CA $585 total
includes taxes & fees
Mar 30 - Mar 31
9/10 Wonderful! (748 reviews)
"Beautiful. Amazing staff. Amazing amenities."

Reviewed on Mar. 20, 2025

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
The price is CA $242 per night from Mar. 27 to Mar. 28
CA $242
CA $334 total
includes taxes & fees
Mar 27 - Mar 28
9.2/10 Wonderful! (474 reviews)
"Enjoyed our stay for 2 nights, off season. Best time to visit Chatham. Not crowded and not noisy."

Reviewed on Mar. 23, 2025

Chatham Wayside Inn
Chatham Seafarer Inn
Chatham Seafarer Inn
3.5 out of 5
2079 Main St, Chatham, MA
9/10 Wonderful! (285 reviews)
"I really liked my stay at the Seafarer! Such a cute spot and the people were super nice. I was in town visiting family, so my room was the perfect convenience with a cute little spot to sit outside my room and sip coffee in the morning and watch the world go by. The bed was comfortable, and it was ..."

Reviewed on Oct. 7, 2024

Get rates
Chatham Seafarer Inn
See all 4,794 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chatham vacation package cost?
Offering excellent value package deals from CA $866 on Expedia, you’ll be pleasantly surprised at how much a vacation 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 vacation packages. Choosing to travel in quieter periods means you’ll typically find better prices on accommodations and flights.
How many days is enough for Chatham?
We’d recommend booking a Chatham vacation 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 neighborhoods like South Chatham and South Harwich. You could even squeeze in one or two day trips beyond Chatham.
Is it worth booking a vacation package to Chatham?
Chatham has everything you need for a wonderful escape. Begin your Chatham vacation 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 vacation as a package?
An Expedia vacation 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 vacation 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 customized Chatham vacation package.

Discover the most popular places to visit in Chatham

Chatham Drama Guild

You can enjoy a show at Chatham Drama Guild during your trip to Chatham. Wander the area's beautiful beaches or simply enjoy one of its seafood restaurants.

Chatham Drama Guild

Veterans Field

Catch an event at Veterans Field during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

Veterans Field

Monomoy Theatre

You can get tickets for a performance at Monomoy Theatre during your trip to Chatham. Wander the beautiful beaches and seaside in the area.

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