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

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$1,118 per night from 1 Dec to 2 Dec
AU$1,118
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
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!
Save an average of 15% on thousands of hotels when you're signed in
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
Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 419-B

Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 419-B

Brewster
With a stay at this vacation home in Brewster (West Brewster), you'll be within a 5-minute drive of Cape Cod Museum of Natural History and Paine's Creek ...
Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 419-B
Walk to bike trail, sleeps 6 w/ 2 kings! AC, nearby bay and ocean beaches

Walk to bike trail, sleeps 6 w/ 2 kings! AC, nearby bay and ocean beaches

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, within a 10-minute drive of Cape Cod National Seashore and Edward Penniman House and ...
Walk to bike trail, sleeps 6 w/ 2 kings! AC, nearby bay and ocean beaches
Panoramic Water Views w/ Private Beach!

Panoramic Water Views w/ Private Beach!

Chatham
A stay at this vacation home places you in the heart of Chatham, steps from Monomoy National Wildlife Refuge and 3 minutes by foot from Cape Cod Beaches.
Panoramic Water Views w/ Private Beach!
5BR  Comfortable, Spacious South Yarmouth  Family Retreat

5BR Comfortable, Spacious South Yarmouth Family Retreat

Yarmouth
When you stay at this vacation home in South Yarmouth, you'll be by the sea, within a 5-minute drive of Cultural Center of Cape Cod and Bass River Golf ...
5BR Comfortable, Spacious South Yarmouth Family Retreat
East Orleans - walk to Nauset Beach

East Orleans - walk to Nauset Beach

Orleans
With a stay at this vacation home in Orleans (East Orleans), you'll be within a 15-minute drive of Cape Cod National Seashore and Cape Cod Beaches.
East Orleans - walk to Nauset Beach
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
1964 Holiday Homes
Lowest Price
AU$286
Highest Price
AU$1,118
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, Heart of Brewster .5 Miles to Beach!, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Magnificent Mansion, Privacy, Pool, Water Views in Brewster; 419-B, Walk to bike trail, sleeps 6 w/ 2 kings! AC, nearby bay and ocean beaches, Panoramic Water Views w/ Private Beach!, 5BR Comfortable, Spacious South Yarmouth Family Retreat, East Orleans - walk to Nauset Beach

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$432 per night from 2 Dec to 3 Dec
AU$432
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
Harbor Hotel Provincetown

Harbor Hotel Provincetown

3 out of 5
698 Commercial St, Provincetown, MA
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
Crowne Pointe Historic Inn & Spa - Adults Only

Crowne Pointe Historic Inn & Spa - Adults Only

4 out of 5
82 Bradford Street, Provincetown, MA
Fully refundableReserve now, pay when you stay
The price is AU$286 per night from 24 Nov to 25 Nov
AU$286
includes taxes & fees
24 Nov - 25 Nov
With a stay at Crowne Pointe Historic Inn & Spa - Adults Only, you'll be centrally located in Provincetown, within a 5-minute drive of Cape Cod National Seashore ...
Crowne Pointe Historic Inn & Spa - Adults Only
Save an average of 15% on thousands of hotels when you're signed in
The Mansion at Ocean Edge

The Mansion at Ocean Edge

4 out of 5
2907 Main Street, Brewster, MA
The price is AU$395 per night from 22 Dec to 23 Dec
AU$395
includes taxes & fees
22 Dec - 23 Dec
With a stay at The Mansion at Ocean Edge in Brewster, you'll be on the waterfront, within a 15-minute drive of Cape Cod National Seashore and Cape Cod ...
The Mansion at Ocean Edge
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.