Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

Darling Cape Cottage - Steps from Downtown Harwich Port

Darling Cape Cottage - Steps from Downtown Harwich Port

Harwich MA
This vacation home is in the heart of Harwich Port, within a 10-minute walk of Bank Street Beach and Cape Cod Beaches.
Opens in a new windowDarling Cape Cottage - Steps from Downtown Harwich Port
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 MA
The price is AU$452 per night from 31 Mar to 1 Apr
AU$452
31 Mar - 1 Apr
includes taxes & fees
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Cape Cod Beaches and Mayflower Beach.
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!

SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!

Yarmouth MA
With a stay at this vacation home, you'll be centrally located in West Yarmouth, within a 5-minute drive of Cape Cod Beaches and Hyannis Harbor.
Opens in a new windowSANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!
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Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

Dennis MA
When you stay at this vacation home in Dennis Port, you'll be on the beach, within a 15-minute drive of Cape Cod Beaches and Hyannis Harbor.
Opens in a new windowStunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!
WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

Yarmouth MA
The price is AU$1,007 per night from 2 Apr to 3 Apr
AU$1,007
2 Apr - 3 Apr
includes taxes & fees
Located in South Yarmouth (Bass River), this vacation home is within a 10-minute drive of Cape Cod Beaches and Hyannis Harbor.
Opens in a new windowWATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham MA
The price is AU$1,005 per night from 14 Apr to 15 Apr
AU$1,005
14 Apr - 15 Apr
includes taxes & fees
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 ...
Opens in a new windowSand Bar-Dog Friendly on Cooks Brook Beach
✸Private Sandy Beach✸ Nantucket Sound 2 Min Walk! Kayak & SUP, Near Harbor &Town

✸Private Sandy Beach✸ Nantucket Sound 2 Min Walk! Kayak & SUP, Near Harbor &Town

Hyannis MA
A stay at this vacation home places you in the heart of Hyannis, a short 3-minute walk from Cape Cod Beaches and within 3 minutes by car from Hyannis ...
Opens in a new window✸Private Sandy Beach✸ Nantucket Sound 2 Min Walk! Kayak & SUP, Near Harbor &Town
Eazy Breezy Beach Home

Eazy Breezy Beach Home

Dennis MA
The price is AU$431 per night from 14 Apr to 15 Apr
AU$431
14 Apr - 15 Apr
includes taxes & fees
With a stay at this vacation home in Dennis Port, you'll be within a 15-minute drive of Cape Cod Beaches and Mayflower Beach.
Opens in a new windowEazy Breezy Beach Home
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham MA
When you stay at this vacation home in Eastham, you'll be by the sea, a 2-minute drive from Cape Cod Beaches and 5 minutes from Cape Cod National Seashore.
Opens in a new windowBeau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
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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
2470 Holiday Homes
Lowest Price
AU$238
Highest Price
AU$1,007
Popular accommodation
Darling Cape Cottage - Steps from Downtown Harwich Port, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!, Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!, WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed, Sand Bar-Dog Friendly on Cooks Brook Beach, ✸Private Sandy Beach✸ Nantucket Sound 2 Min Walk! Kayak & SUP, Near Harbor &Town, Eazy Breezy Beach Home, Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AU$603 per night from 18 Mar to 19 Mar
AU$603
18 Mar - 19 Mar
includes taxes & fees
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.
Opens in a new windowChatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 22 Mar to 23 Mar
AU$238
22 Mar - 23 Mar
includes taxes & fees
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.
Opens in a new windowChatham Wayside Inn
Captain's House Inn

Captain's House Inn

4 out of 5
369 Old Harbor Road Chatham MA
When you stay at Captain's House Inn in Chatham, you'll be near the beach, within a 10-minute walk of Cape Cod Beaches and Chatham Shark Center.
Opens in a new windowCaptain's House Inn
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Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St Chatham MA
When you stay at Surfside Inn Chatham in Chatham, you'll be on the waterfront, within a 5-minute walk of Cape Cod Beaches and Chatham Lighthouse Beach.
Opens in a new windowSurfside Inn Chatham
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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.