Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

Renovated cottage 1 mile to beach in Chatham!

Renovated cottage 1 mile to beach in Chatham!

Chatham
Stay at this vacation home in Chatham. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Ridgevale Beach and Hardings Beach are ...
Opens in a new windowRenovated cottage 1 mile to beach in Chatham!
Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod

Barnstable
The price is NZ$1,042 per night from 18 Sept to 19 Sept
NZ$1,042
18 Sept - 19 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.
Opens in a new windowHyannis Hideaway in 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$524 per night from 22 Sept to 23 Sept
NZ$524
22 Sept - 23 Sept
includes taxes & fees
Stay at this vacation home in Dennis Port. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Cape Cod Theatre Company – Home of the ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
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Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

Barnstable
Book a stay at this family-friendly vacation home in Hyannis. Enjoy free WiFi, private pools, and a water park. Popular attractions Hyannis Harbor and Keyes ...
Opens in a new windowBrand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2 out of 5
Brewster
The price is NZ$1,273 per night from 8 Oct to 9 Oct
NZ$1,273
8 Oct - 9 Oct
includes taxes & fees
Stay at this vacation home in Brewster. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Sheep Pond and Cape Cod Museum of Natural History ...
Opens in a new windowCoastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail

Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, laundry facilities, and patios. Popular attractions Nauset Beach and Cape Cod National Seashore are located ...
Opens in a new windowCape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail
Charming Classic Cape Home Bordering Bike Trail-Family Friendly In Harwich

Charming Classic Cape Home Bordering Bike Trail-Family Friendly In Harwich

Harwich
Book a stay at this family-friendly vacation home in Harwich. Enjoy free WiFi, a water park, and a garden. Popular attractions Cape Cod Lavender Farm and Cranberry ...
Opens in a new windowCharming Classic Cape Home Bordering Bike Trail-Family Friendly In Harwich

HARWICH PORT SPECIAL PLACE inquire about long-term

HARWICH PORT SPECIAL PLACE inquire about long-term

Harwichport
Book a stay at this golf vacation home in Harwich Port. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Harwich Port and Bank Street Beach ...
Opens in a new window HARWICH PORT SPECIAL PLACE inquire about long-term
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
Book a stay at this beach vacation home in Chatham. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Hardings Beach and ...
Opens in a new windowBreathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
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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$524
Highest Price
NZ$1,273
Popular accommodation
Renovated cottage 1 mile to beach in Chatham!, Hyannis Hideaway in Cape Cod, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail, Charming Classic Cape Home Bordering Bike Trail-Family Friendly In Harwich, HARWICH PORT SPECIAL PLACE inquire about long-term , Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$847 per night from 6 Oct to 7 Oct
NZ$847
6 Oct - 7 Oct
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 ...
Opens in a new windowChatham 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 ...
Opens in a new windowChatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
Stay at this 3-star family-friendly motel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowGreyfinch Chatham Inn
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Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
Stay at this 4-star spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
Opens in a new windowMargaritaville Resort Cape Cod
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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.