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
Stay at this holiday home in Harwich Port. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bank Street Beach and Harwich Port are located ...
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 NZ$515 per night from 31 Mar to 1 Apr
NZ$515
31 Mar - 1 Apr
includes taxes & fees
Stay at this holiday home in Dennis Port. Enjoy free Wi-Fi, laundry facilities and balconies or patios. Popular attractions Cape Cod Theatre Company – Home of ...
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
Stay at this family-friendly holiday home in West Yarmouth. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hyannis Harbor and Wild Animal ...
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
Stay at this beach holiday home in Dennis Port. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Haigis Beach and Swan Pond River are ...
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 NZ$1,193 per night from 17 Apr to 18 Apr
NZ$1,193
17 Apr - 18 Apr
includes taxes & fees
Stay at this beach holiday home in South Yarmouth. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Hyannis Harbor and Cultural Center of Cape ...
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 NZ$883 per night from 22 Mar to 23 Mar
NZ$883
22 Mar - 23 Mar
includes taxes & fees
Stay at this beach holiday home in Eastham. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Cooks Brook Beach and Sunken Meadow ...
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
Stay at this family-friendly holiday home in Hyannis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hyannis Harbor and Keyes Memorial ...
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 NZ$469 per night from 22 Mar to 23 Mar
NZ$469
22 Mar - 23 Mar
includes taxes & fees
Stay at this holiday home in Dennis Port. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Cape Cod Theatre Company – Home of the Harwich ...
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
The price is NZ$888 per night from 20 Apr to 21 Apr
NZ$888
20 Apr - 21 Apr
includes taxes & fees
Stay at this holiday home in Eastham. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Cooks Brook Beach and Sunken Meadow Beach are located ...
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
NZ$469
Highest Price
NZ$1,193
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 NZ$722 per night from 25 Mar to 26 Mar
NZ$722
25 Mar - 26 Mar
includes taxes & fees
Stay at this luxury resort in Chatham. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the property condition in ...
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
Stay at this golf hotel in Chatham. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. ...
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
Stay at this B&B in Chatham. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Chatham Shark Center and Chatham Seaside Links are located ...
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
Stay at this beach B&B in Chatham. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Chatham Lighthouse and Chatham Windmill are located ...
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.