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Chatham Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chatham vacation homes are the perfect way for you to wing it.

Holiday houses in Chatham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chatham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chatham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chatham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chatham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chatham Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$215
Highest Price
AU$640
Popular accommodation
Chatham Bars Inn, Chatham Wayside Inn, Chatham Seafarer Inn, Bayside Resort Hotel

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is AU$640 per night from 15 Jan to 16 Jan
AU$640
includes taxes & fees
15 Jan - 16 Jan
When you a stay at Chatham Bars Inn in Chatham, you'll be on the boardwalk/promenade, within a 5-minute walk of Chatham Seaside Links and Cape Cod Beaches.
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
The price is AU$374 per night from 9 Jan to 10 Jan
AU$374
includes taxes & fees
9 Jan - 10 Jan
When you a stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, just steps from Mayo House and Gallery Antonia.
Chatham Wayside Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

3.5 out of 5
2079 Main St, Chatham, MA
Located in Chatham, Chatham Seafarer Inn is a 5-minute drive from Harwich Port and 11 minutes from Nickerson State Park.
Chatham Seafarer Inn
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Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 21 Jan to 22 Jan
AU$215
includes taxes & fees
21 Jan - 22 Jan
With a stay at Bayside Resort Hotel in West Yarmouth, you'll be near the bay, just a 1-minute walk from Main Street and 8 minutes by foot from Putter's Paradise ...
Bayside Resort Hotel
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.