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.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
per person
Dec. 20 - Dec. 24
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.2/10 Good! (386 reviews)
The room was very old and not real clean in corners. No outlet in bathroom. Not very convenient to downtown. Would be afraid to walk around after dark as a single woman.

Reviewed on Nov. 4, 2024

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Dec. 22 - Dec. 27
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (228 reviews)
Beautiful hotel and extremely pleasant staff.

Reviewed on Oct. 12, 2024

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Dec. 22 - Dec. 27
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (64 reviews)
Excellent hotel. The only thing was that the AC in our room was so loud when turned on that it was unbearable. The hotel did help us move to another room that did not have the problem. We were only there for a night. We will definitely stay again as it is an excellent hotel otherwise.

Reviewed on Oct. 27, 2024

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Jan. 6 - Jan. 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Wonderful stay at the Boston Harbor Hotel - rooms, service, and amenities are great. And the location on the harbor is beautiful and convenient.

Reviewed on Nov. 4, 2024

The Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
per person
Dec. 31 - Jan. 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (1,000 reviews)
Everything was good except for the fact that cleaning staff forgot to turn off the clock alarm and so we were awakened way before we wanted to get up at 6 AM! The only other issue was that the toilet seat needed to be held up, and would not stay up on its own. Everything else was fine. And we were happy to discover the Boston public library across the street. It’s a great place to visit.

Reviewed on Nov. 3, 2024

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 $425 per night from Nov. 6 to Nov. 7
CA $425
CA $511 total
includes taxes & fees
Nov 6 - Nov 7
9/10 Wonderful! (728 reviews)
"Location, service, food, and amenities are all top notch. The complimentary limo service needs extra mention as it was impeccable: brand new cars, local drivers, fast and reliable. Made for a very enjoyable stay. Thanks"

Reviewed on Nov. 2, 2024

Chatham Bars Inn
Chatham Wayside Inn
Chatham Wayside Inn
4 out of 5
512 Main St, Chatham, MA
The price is CA $277 per night from Nov. 6 to Nov. 7
CA $277
CA $372 total
includes taxes & fees
Nov 6 - Nov 7
9.2/10 Wonderful! (444 reviews)
"Fabulous hotel in a beautiful location."

Reviewed on Oct. 31, 2024

Chatham Wayside Inn
Chatham Seafarer Inn
Chatham Seafarer Inn
3.5 out of 5
2079 Main St, Chatham, MA
9/10 Wonderful! (284 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 4,726 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?
Discover the best of Chatham from as little as CA $745. Choose from a great selection of flights, rental cars and hotels to suit every style and budget. You can pick up even more discounts when you add some sightseeing activities to your vacation package.
How do I get a cheap travel package to Chatham?
Booking a flight and hotel together with Expedia won’t just save you time — it’ll save you a tidy sum too. A Chatham vacation package makes it a cinch to organize your dream adventure. With more than 550 airlines all over the world to select from, finding convenient flights that suit your schedule won’t be hard. In addition to that, we have over 1,000,000 hotels globally to select from. Now that’s choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Chatham?
Close to the action. Many visitors like to book hotels in the vicinity of popular attractions, such as Chatham Lighthouse, Chatham Lighthouse Beach and Chatham Fish Pier.
What are the top hotels in Chatham?
Book a room at Cute Clapboard Cottage On The Hill Off Stage Island Road. It’s one of the area’s most in-demand properties. Another well-known option in Chatham is Colorful Clapboard Cottage Perfect For 2.
How far in advance should I book my Chatham vacation?
It all depends on the air carrier, but you can generally compare international fares on Expedia up to 12 months in advance. While it’s a good idea to book ahead of time, lucky customers occasionally nab a cheaper flight only weeks before their intended journey.
What does an Expedia Chatham travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your ideal Chatham travel package. Once you’ve made your booking, you can add on fun stuff like tours and experiences. Remember — the more you bundle, the greater the savings!
Can I choose my airline with a Chatham Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines all over the world, so select the carrier that fits your travel needs.
If I'm not able to travel, can I cancel my Chatham vacation package?
Don’t stress if you’re rethinking your Chatham vacation package — you can cancel or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We get that life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.

Discover the most popular places to visit in Chatham

Image for Veterans Field

Veterans Field

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

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