Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

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$562 per night from 1 Nov to 2 Nov
AU$562
1 Nov - 2 Nov
includes taxes & fees
With a stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Mayflower Beach and Cape Cod Theatre Company – Home of the ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2 out of 5
Brewster
The price is AU$1,076 per night from 20 Oct to 21 Oct
AU$1,076
20 Oct - 21 Oct
includes taxes & fees
With a stay at this vacation home in Brewster (West Brewster), you'll be within a 15-minute drive of Cape Cod Beaches and Sheep Pond.
Opens in a new windowCoastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

2 out of 5
Yarmouth
With a stay at this vacation home in South Yarmouth, you'll be within a 15-minute drive of Hyannis Harbor and Mayflower Beach.
Opens in a new windowMid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard
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Oceanfront Escape house on SeaView Beach, Dog-Friendly!

Oceanfront Escape house on SeaView Beach, Dog-Friendly!

South Yarmouth
With a stay at this vacation home in South Yarmouth (Bass River), you'll be steps from Thachers Beach and a 1-minute drive from Gold Coast Parasailing & Jet ...
Opens in a new windowOceanfront Escape house on SeaView Beach, Dog-Friendly!
Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Chatham
Located in West Chatham, this vacation home is by the sea, within a 5-minute drive of Ridgevale Beach and Chatham Chamber of Commerce.
Opens in a new windowSpacious, private cottage just a few minutes walk to Ridgevale Beach!
Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Cape Cod National Seashore and Campground Beach.
Opens in a new windowSteps to a private bay beach from this private & Charming Cape! Book this Fall!
Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
A stay at this vacation home places you in the heart of Chatham, within a 5-minute walk of Mayo House and Gallery Antonia.
Opens in a new windowDowntown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
Located in Chatham, this vacation home is by the sea, within a 5-minute drive of Hardings Beach and Monomoy Theatre.
Opens in a new windowBreathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Barnstable
The price is AU$1,088 per night from 19 Oct to 20 Oct
AU$1,088
19 Oct - 20 Oct
includes taxes & fees
When you stay at this vacation home in Hyannis, you'll be on the waterfront, within a 10-minute walk of Hyannis Harbor and Main Street Hyannis.
Opens in a new windowCharming Hyannis 3 Bed 2 Bath
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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
2582 Holiday Homes
Lowest Price
AU$408
Highest Price
AU$1,088
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard, Oceanfront Escape house on SeaView Beach, Dog-Friendly!, Spacious, private cottage just a few minutes walk to Ridgevale Beach!, Steps to a private bay beach from this private & Charming Cape! Book this Fall!, Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Charming Hyannis 3 Bed 2 Bath

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is AU$698 per night from 20 Oct to 21 Oct
AU$698
20 Oct - 21 Oct
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
When you a stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, just steps from Mayo House and Gallery Antonia.
Opens in a new windowChatham Wayside Inn
Greyfinch Chatham Inn

Greyfinch Chatham Inn

3 out of 5
946 Main Street (Rte 28), Chatham, MA
Located in Chatham, Greyfinch Chatham Inn is in the historical district, within a 5-minute drive of Atwood House Museum and Chatham Shark Center.
Opens in a new windowGreyfinch Chatham Inn
Save an average of 15% on thousands of hotels when you're signed in
The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd, Chatham, MA
The price is AU$408 per night from 19 Oct to 20 Oct
AU$408
19 Oct - 20 Oct
includes taxes & fees
When you stay at The Hawthorne in Chatham, you'll be on the beach, within a 15-minute walk of Chatham Seaside Links and Mayo House.
Opens in a new windowThe Hawthorne
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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.