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
The price is AU$710 per night from 5 May to 6 May
AU$710
includes taxes & fees
5 May - 6 May
With a stay at this vacation home in Chatham, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Hardings Beach.
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
Located in South Yarmouth (Bass River), this vacation home is within a 10-minute drive of Cape Cod Beaches and Hyannis Harbor.
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
The price is AU$1,019 per night from 27 Apr to 28 Apr
AU$1,019
includes taxes & fees
27 Apr - 28 Apr
When you stay at this vacation home in Eastham, you'll be on the beach, a 1-minute drive from Cape Cod Beaches and 6 minutes from Cape Cod National ...
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
When you stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Cape Cod National Seashore.
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
With a stay at this vacation home in South Yarmouth (Bass River), you'll be a 1-minute drive from Cape Cod Beaches and 8 minutes from Hyannis Harbor.
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
When you stay at this vacation home in Eastham, you'll be by the sea, a 4-minute drive from Cape Cod National Seashore and 8 minutes from Cape Cod Beaches.
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 AU$496 per night from 11 May to 12 May
AU$496
includes taxes & fees
11 May - 12 May
When you stay at this vacation home in Dennis Port, you'll be by the sea, a 2-minute drive from Cape Cod Beaches and 5 minutes from West Dennis Beach.
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
When you stay at this vacation home in South Yarmouth, you'll be by the sea, within a 10-minute drive of Cape Cod Beaches and West Dennis Beach.
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
With a stay at this vacation home, you'll be centrally located in Chatham, within a 5-minute drive of Cape Cod Beaches and Gallery Antonia.
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
2517 Holiday Homes
Lowest Price
AU$429
Highest Price
AU$1,019
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 AU$709 per night from 1 May to 2 May
AU$709
includes taxes & fees
1 May - 2 May
When you stay at Chatham Bars Inn in Chatham, you'll be on the boardwalk/promenade, within a 5-minute walk of Cape Cod Beaches and Chatham Seaside Links.
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
The price is AU$438 per night from 23 Apr to 24 Apr
AU$438
includes taxes & fees
23 Apr - 24 Apr
When you stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, within a 15-minute walk of Cape Cod Beaches and Gallery Antonia.
Chatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
The price is AU$429 per night from 2 May to 3 May
AU$429
includes taxes & fees
2 May - 3 May
Located in Chatham, Greyfinch Chatham Inn is in the historical district, within a 5-minute drive of Atwood House Museum and Chatham Shark Center.
Greyfinch Chatham Inn
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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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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.