Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

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

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

2 out of 5
Brewster
The price is AU$1,119 per night from 1 Dec to 2 Dec
AU$1,119
includes taxes & fees
1 Dec - 2 Dec
With a stay at this vacation home in Brewster (West Brewster), you'll be a 2-minute drive from Sheep Pond and 5 minutes from Rail Trail Bike Shop.
Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!
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
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 5-minute drive of Cape Cod Theatre Company – Home of the Harwich Jr. Theatre ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Cozy Cape home with outdoor shower and deck - minutes to beach

Cozy Cape home with outdoor shower and deck - minutes to beach

Barnstable
When you stay at this vacation home in Hyannis, you'll be by the sea, within a 5-minute drive of Cape Cod Melody Tent and St. Francis Xavier Church.
Cozy Cape home with outdoor shower and deck - minutes to beach
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Heart of Brewster .5 Miles to Beach!

Heart of Brewster .5 Miles to Beach!

Brewster
Located in Brewster, this vacation home is by the sea, within a 15-minute walk of Cape Cod Beaches and Breakwater Beach.
Heart of Brewster .5 Miles to Beach!
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
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 5-minute drive of Bass River Sports World and Cultural Center of Cape ...
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

Barnstable
With a stay at this vacation home in Centerville, you'll be within a 5-minute drive of Barnstable Performing Arts Center and Cape Cod Beaches.
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

West Yarmouth
Located in West Yarmouth, this vacation home is by the sea, within a 5-minute drive of Cape Cod Beaches and Cape Cod Inflatable Park.
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill

Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill

Yarmouth
A stay at this vacation home places you in the heart of West Yarmouth, within a 5-minute drive of Cape Cod Beaches and Cape Cod Inflatable Park.
Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill
✸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
With a stay at this vacation home, you'll be centrally located in Hyannis, just a 3-minute walk from Cape Cod Beaches and 9 minutes by foot from Keyes Memorial ...
✸Private Sandy Beach✸ Nantucket Sound-2 Min Walk! Kayak & SUP, Near Harbor &Town
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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
2226 Holiday Homes
Lowest Price
AU$121
Highest Price
AU$1,119
Popular accommodation
Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Cozy Cape home with outdoor shower and deck - minutes to beach, Heart of Brewster .5 Miles to Beach!, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!, Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach, Pristine bungalow with amazing walkable location - fast WiFi, firepit, & grill, ✸Private Sandy Beach✸ Nantucket Sound-2 Min Walk! Kayak & SUP, Near Harbor &Town

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is AU$433 per night from 2 Dec to 3 Dec
AU$433
includes taxes & fees
2 Dec - 3 Dec
When you a stay at Chatham Bars Inn in Chatham, you'll be on the boardwalk/promenade, within a 5-minute walk of Chatham Seaside Links and Cape Cod Beaches.
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
With a stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, just a 1-minute walk from Mayo House and 7 minutes by foot from Chatham ...
Chatham Wayside Inn
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 10 minutes from Chatham Lighthouse Beach.
Chatham Seafarer Inn
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Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$121 per night from 25 Nov to 26 Nov
AU$121
includes taxes & fees
25 Nov - 26 Nov
Located in West Yarmouth, Cape Sands Inn is near the bay, within a 5-minute drive of John F. Kennedy Hyannis Museum and Cape Cod Inflatable Park.
Cape Sands Inn
Don't see what you're looking for?
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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.