Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
Stay at this vacation home in Chatham. Enjoy a water park, a garden, and patios. Popular attractions Hardings Beach and Ridgevale Beach are located nearby.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

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 Cape Cod ...
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham
Book a stay at this beach vacation home in Eastham. Enjoy free WiFi, a beach locale, and patios. Popular attractions Cape Cod National Seashore and Cooks Brook ...
Sand Bar-Dog Friendly on Cooks Brook Beach
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Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Herring Brook Beach and Thumpertown Beach are ...
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

west yarmouth, Cape Cod
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 Cape Cod ...
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, laundry facilities, and patios. Popular attractions Cape Cod National Seashore and Poit's Lighthouse Mini ...
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
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 11 May to 12 May
NZ$524
includes taxes & fees
11 May - 12 May
Stay at this vacation home in Dennis Port. Enjoy free WiFi, a water park, and balconies or patios. Popular attractions Cape Cod Theatre Company – Home of the ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Waterfront, Incredible Views and Private Dock!

Waterfront, Incredible Views and Private Dock!

Yarmouth
Stay at this vacation home in South Yarmouth. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Cape Cod Rail Trail and Bass River ...
Waterfront, Incredible Views and Private Dock!
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham
Book a stay at this family-friendly vacation home in Chatham. Enjoy free WiFi, a garden, and furnished patios. Popular attractions Chatham Railroad Museum and ...
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
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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
2511 Holiday Homes
Lowest Price
NZ$329
Highest Price
NZ$762
Popular accommodation
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Sand Bar-Dog Friendly on Cooks Brook Beach, Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach, OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR, Secluded home with firepit, & scenic yard - near Nauset Beach & shops, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Waterfront, Incredible Views and Private Dock!, Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$762 per night from 1 May to 2 May
NZ$762
includes taxes & fees
1 May - 2 May
Book a stay at this 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
The price is NZ$468 per night from 20 Apr to 21 Apr
NZ$468
includes taxes & fees
20 Apr - 21 Apr
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
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. ...
Greyfinch Chatham Inn
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Chatham Seafarer Inn

Chatham Seafarer Inn

3.5 out of 5
2079 Main St, Chatham, MA
The price is NZ$329 per night from 1 May to 2 May
NZ$329
includes taxes & fees
1 May - 2 May
Stay at this 3.5-star hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cockle Cove Beach and Ridgevale Beach are located ...
Chatham Seafarer Inn
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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.