Book Holiday Homes in South Wellfleet

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 Wellfleet

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
The price is AU$706 per night from 16 Apr to 17 Apr
AU$706
includes taxes & fees
16 Apr - 17 Apr
With a stay at this vacation home in Chatham, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Hardings Beach.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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
Located in South Yarmouth (Bass River), this vacation home is within a 10-minute drive of Cape Cod Beaches and Hyannis Harbor.
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham
The price is AU$883 per night from 6 Apr to 7 Apr
AU$883
includes taxes & fees
6 Apr - 7 Apr
When you stay at this vacation home in Eastham, you'll be on the beach, a 1-minute drive from Cape Cod Beaches and 6 minutes from Cape Cod National ...
Sand Bar-Dog Friendly on Cooks Brook Beach
Save an average of 15% on thousands of hotels when you're signed in
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Eastham
When you stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Cape Cod National Seashore.
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Eastham
When you stay at this vacation home in Eastham, you'll be by the sea, a 4-minute drive from Cape Cod National Seashore and 8 minutes from Cape Cod Beaches.
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
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, a 2-minute drive from Cape Cod Beaches and 5 minutes from West Dennis Beach.
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Waterfront, Incredible Views and Private Dock!

Waterfront, Incredible Views and Private Dock!

Yarmouth
When you stay at this vacation home in South Yarmouth, you'll be by the sea, within a 10-minute drive of Cape Cod Beaches and West Dennis Beach.
Waterfront, Incredible Views and Private Dock!
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham
With a stay at this vacation home, you'll be centrally located in Chatham, within a 5-minute drive of Cape Cod Beaches and Chatham Shark Center.
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

Dennis
With a stay at this vacation home in Dennis Port, you'll be on the beach, steps from Cape Cod Beaches and a 3-minute drive from West Dennis Beach.
Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista
Don't see what you're looking for?
See all available properties in South Wellfleet
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 Wellfleet 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 Wellfleet vacation homes are the perfect way for you to wing it.

Holiday houses in South Wellfleet 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 Wellfleet 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 Wellfleet adventures, obvs.

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

Accommodation
2220 Holiday Homes
Lowest Price
AU$276
Highest Price
AU$883
Popular accommodation
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Sand Bar-Dog Friendly on Cooks Brook Beach, Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach, Secluded home with firepit, & scenic yard - near Nauset Beach & shops, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Waterfront, Incredible Views and Private Dock!, Unique Oyster Pond 3bd-2ba home in private setting close to downtown., Stunning Oceanfront Home With Amazing Views ~ Private Beach - capeoceanvista

Top trending hotels in South Wellfleet

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is AU$719 per night from 1 May to 2 May
AU$719
includes taxes & fees
1 May - 2 May
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.
Chatham Bars Inn
The Provincetown Inn

The Provincetown Inn

3 out of 5
1 Commercial Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 17 Apr to 18 Apr
AU$276
includes taxes & fees
17 Apr - 18 Apr
When you stay at The Provincetown Inn in Provincetown, you'll be on the beach, just steps from Commercial Street and Cape Cod Beaches.
The Provincetown Inn
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 17 Apr to 18 Apr
AU$276
includes taxes & fees
17 Apr - 18 Apr
Located in Provincetown, Harbor Hotel Provincetown is on the waterfront, within a 5-minute drive of Race Point Beach and MacMillan Pier.
Harbor Hotel Provincetown
Save an average of 15% on thousands of hotels when you're signed in
Edgewater Beach Resort, a VRI resort

Edgewater Beach Resort, a VRI resort

3.5 out of 5
95 Chase Avenue, Dennis Port, MA
With a stay at Edgewater Beach Resort, a VRI resort in Dennis Port, you'll be a 1-minute drive from Cape Cod Beaches and 6 minutes from West Dennis Beach.
Edgewater Beach Resort, a VRI resort
Don't see what you're looking for?
See all available properties in South Wellfleet
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.