Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

3 Mi to Beach: Historic Farmhouse on Cape Cod!

3 Mi to Beach: Historic Farmhouse on Cape Cod!

South Dennis
Stay at this vacation home in South Dennis. Enjoy a garden, laundry facilities, and patios. Popular attractions Mayflower Beach and Jericho House and Barn Museum ...
3 Mi to Beach: Historic Farmhouse on Cape Cod!
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
The price is NZ$631 per night from 14 Aug to 15 Aug
NZ$631
14 Aug - 15 Aug
includes taxes & fees
Stay at this vacation home in Dennis Port. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Cape Cod Inflatable Park and Cape Cod Theatre ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Great Home Close to Craigville Beach

Great Home Close to Craigville Beach

Barnstable
Stay at this vacation home in Centerville. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Hyannis Harbor and Craigville ...
Great Home Close to Craigville Beach
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Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Chatham
Stay at this vacation home in Chatham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Chatham Drama Guild and Monomoy Theatre are located ...
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod

Barnstable
The price is NZ$1,429 per night from 2 Sept to 3 Sept
NZ$1,429
2 Sept - 3 Sept
includes taxes & fees
Stay at this vacation home in Hyannis. Enjoy free WiFi and air conditioning. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Hyannis Hideaway in Cape Cod
Waterfront escape with gas grill, furnished deck, fast WiFi, beach access nearby

Waterfront escape with gas grill, furnished deck, fast WiFi, beach access nearby

Dennis Port
Stay at this vacation home in Dennis Port. Enjoy a garden, laundry facilities, and patios. Popular attractions Mayflower Beach and Cape Cod Rail Trail are located ...
Waterfront escape with gas grill, furnished deck, fast WiFi, beach access nearby
Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!

Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!

Brewster
Stay at this vacation home in Brewster. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ocean Edge Golf Club and Rail Trail Bike Shop ...
Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!
CONTEMPORARY RANCH STYLE HOME, CLOSE TO CRAIGVILLE BEACH AREA

CONTEMPORARY RANCH STYLE HOME, CLOSE TO CRAIGVILLE BEACH AREA

Barnstable
Stay at this vacation home in Centerville. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Cape Codder Water Park and Hyannis Harbor ...
CONTEMPORARY RANCH STYLE HOME, CLOSE TO CRAIGVILLE BEACH AREA
Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

2 out of 5
Yarmouth
Stay at this vacation home in South Yarmouth. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor ...
Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views
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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.

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
2717 Holiday Homes
Lowest Price
NZ$309
Highest Price
NZ$1,597
Popular accommodation
3 Mi to Beach: Historic Farmhouse on Cape Cod!, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Great Home Close to Craigville Beach, Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants, Hyannis Hideaway in Cape Cod, Waterfront escape with gas grill, furnished deck, fast WiFi, beach access nearby, Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!, CONTEMPORARY RANCH STYLE HOME, CLOSE TO CRAIGVILLE BEACH AREA, Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$1,597 per night from 1 Sept to 2 Sept
NZ$1,597
1 Sept - 2 Sept
includes taxes & fees
Stay at this 5-star luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Chatham Wayside Inn
The Chatham Motel

The Chatham Motel

2 out of 5
1487 Main Street, Chatham, MA
The price is NZ$309 per night from 1 Sept to 2 Sept
NZ$309
1 Sept - 2 Sept
includes taxes & fees
Stay at this motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hardings Beach and Ridgevale Beach are located ...
The Chatham Motel
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The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd, Chatham, MA
The price is NZ$660 per night from 1 Sept to 2 Sept
NZ$660
1 Sept - 2 Sept
includes taxes & fees
Book a stay at this beach hotel in Chatham. Enjoy free WiFi, free parking, and a private beach. Popular attractions Chatham Seaside Links and Mayo House are ...
The Hawthorne
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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.

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^Subject to availability and chosen travel dates.