Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

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$546 per night from 4 Nov to 5 Nov
NZ$546
4 Nov - 5 Nov
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
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$1,124 per night from 18 Nov to 19 Nov
NZ$1,124
18 Nov - 19 Nov
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!
Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

2 out of 5
Yarmouth
Stay at this vacation home in South Yarmouth. Enjoy a garden, laundry facilities, and patios. Popular attractions Hyannis Harbor and Mayflower Beach are located ...
Opens in a new windowMid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard
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Oceanfront Escape house on SeaView Beach, Dog-Friendly!

Oceanfront Escape house on SeaView Beach, Dog-Friendly!

South Yarmouth
Book a stay at this beach vacation home in South Yarmouth. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hyannis Harbor and Gold Coast ...
Opens in a new windowOceanfront Escape house on SeaView Beach, Dog-Friendly!
Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Chatham
Stay at this vacation home in West Chatham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Cockle Cove Beach and Ridgevale Beach are ...
Opens in a new windowSpacious, private cottage just a few minutes walk to Ridgevale Beach!
Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Eastham
Stay at this vacation home in Eastham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Nauset Beach and Cape Cod National Seashore are ...
Opens in a new windowSteps to a private bay beach from this private & Charming Cape! Book this Fall!
Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
Book a stay at this family-friendly vacation home in Chatham. Enjoy free WiFi, private pools, and a garden. Popular attractions Mayo House and Gallery Antonia ...
Opens in a new windowDowntown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
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
Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Barnstable
Stay at this vacation home in Hyannis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hyannis Harbor and Cape Cod Maritime Museum are ...
Opens in a new windowCharming Hyannis 3 Bed 2 Bath
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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
2582 Holiday Homes
Lowest Price
NZ$546
Highest Price
NZ$1,124
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard, Oceanfront Escape house on SeaView Beach, Dog-Friendly!, Spacious, private cottage just a few minutes walk to Ridgevale Beach!, Steps to a private bay beach from this private & Charming Cape! Book this Fall!, Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Charming Hyannis 3 Bed 2 Bath

Top trending hotels in Chatham

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
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$714 per night from 2 Dec to 3 Dec
NZ$714
2 Dec - 3 Dec
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
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St, Chatham, MA
Book a stay at this beach B&B in Chatham. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are ...
Opens in a new windowSurfside Inn Chatham
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The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd, Chatham, MA
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 ...
Opens in a new windowThe 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.