Book Holiday Homes in Chatham

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chatham

Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck

Barnstable MA
The price is NZ$767 per night from 26 May to 27 May
NZ$767
26 May - 27 May
includes taxes & fees
Stay at this holiday home in Hyannis. Enjoy free Wi-Fi, patios and air conditioning. Popular attractions Hyannis Harbor and Main Street Hyannis are located ...
Opens in a new windowCharming 3 bed room with magnificent views & large deck
Eazy Breezy Beach Home

Eazy Breezy Beach Home

Dennis MA
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
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$478 per night from 10 May to 11 May
NZ$478
10 May - 11 May
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
Save an average of 15% on thousands of hotels when you're signed in
450 ft to Raycroft Beach, Game Room, Dog Friendly!

450 ft to Raycroft Beach, Game Room, Dog Friendly!

Dennis MA
Stay at this holiday home in Dennis Port. Enjoy a garden, balconies and an in-room coffee maker. Popular attractions Sea Street Beach and Cape Cod Theatre Company ...
Opens in a new window450 ft to Raycroft Beach, Game Room, Dog Friendly!
Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps  5

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5

South Yarmouth MA
Stay at this beach holiday home in South Yarmouth. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Hyannis Harbor and Main Street Hyannis ...
Opens in a new windowPrivate Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5
Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

Yarmouth Port MA
Stay at this family-friendly holiday home in Yarmouth Port. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Mayflower Beach and Hyannis ...
Opens in a new windowClose to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food
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$864 per night from 13 May to 14 May
NZ$864
13 May - 14 May
includes taxes & fees
Stay at this holiday home in Eastham. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Cape Cod National Seashore and Cooks Brook Beach are ...
Opens in a new windowBeau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!

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

Dennis MA
The price is NZ$2,137 per night from 17 May to 18 May
NZ$2,137
17 May - 18 May
includes taxes & fees
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!
CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

Yarmouth MA
Stay at this family-friendly holiday home in Hyannis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hyannis Harbor and Main Street Hyannis ...
Opens in a new windowCLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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
2394 Holiday Homes
Lowest Price
NZ$469
Highest Price
NZ$2,137
Popular accommodation
Charming 3 bed room with magnificent views & large deck, Eazy Breezy Beach Home, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, 450 ft to Raycroft Beach, Game Room, Dog Friendly!, Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5, Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food, Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!, Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!, CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is NZ$842 per night from 17 May to 18 May
NZ$842
17 May - 18 May
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
The price is NZ$469 per night from 17 May to 18 May
NZ$469
17 May - 18 May
includes taxes & fees
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
Save an average of 15% on thousands of hotels when you're signed in
Queen Anne Inn

Queen Anne Inn

4 out of 5
70 Queen Anne Rd Chatham MA
The price is NZ$506 per night from 2 June to 3 June
NZ$506
2 June - 3 June
includes taxes & fees
Stay at this business-friendly hotel in Chatham. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowQueen Anne Inn
Don't see what you're looking for?
See all available properties in Chatham
View all properties
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.