Book Holiday Homes in South 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 South 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!
4BR Ocean Timberland - Osterville  w/ private pool

4BR Ocean Timberland - Osterville w/ private pool

Barnstable
With a stay at this vacation home in Osterville, you'll be within a 10-minute drive of Stand Up & Paddle Cape Cod and Cotuit Center for the Arts.
4BR Ocean Timberland - Osterville w/ private pool
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
Save an average of 15% on thousands of hotels when you're signed in
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
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
Don't see what you're looking for?
See all available properties in South 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.

South 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 South Chatham vacation homes are the perfect way for you to wing it.

Holiday houses in South 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 South 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 South Chatham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South 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 South 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.

South Chatham Holiday Homes essential information

Accommodation
2262 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$1,119
Popular accommodation
Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!, 4BR Ocean Timberland - Osterville w/ private pool, 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

Top trending hotels in South Chatham

Chatham Tides

Chatham Tides

2.5 out of 5
394 Pleasant St, PO Box 215, South Chatham, MA
The price is AU$266 per night from 25 Nov to 26 Nov
AU$266
includes taxes & fees
25 Nov - 26 Nov
With a stay at Chatham Tides in South Chatham, you'll be on the beach, just a 1-minute walk from Cape Cod Beaches and 11 minutes by foot from Forest Beach.
Chatham Tides
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$131 per night from 25 Nov to 26 Nov
AU$131
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
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 8 Dec to 9 Dec
AU$141
includes taxes & fees
8 Dec - 9 Dec
With a stay at Bayside Resort Hotel in West Yarmouth, you'll be near the bay, just a 1-minute walk from Main Street and 8 minutes by foot from Putter's Paradise ...
Bayside Resort Hotel
Save an average of 15% on thousands of hotels when you're signed in
Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

3 out of 5
476 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 1 Dec to 2 Dec
AU$178
includes taxes & fees
1 Dec - 2 Dec
When you stay at Aiden by Best Western Cape Cod - West Yarmouth in West Yarmouth, you'll be near the beach, within a 5-minute drive of John F. Kennedy Hyannis ...
Aiden by Best Western Cape Cod - West Yarmouth
Don't see what you're looking for?
See all available properties in South 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.