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

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 MA
The price is AU$402 per night from 19 May to 20 May
AU$402
19 May - 20 May
includes taxes & fees
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Cape Cod Beaches and Main Street Hyannis.
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham MA
The price is AU$724 per night from 20 May to 21 May
AU$724
20 May - 21 May
includes taxes & fees
When you stay at this vacation home in Eastham, you'll be by the sea, a 2-minute drive from Cape Cod Beaches and 5 minutes from Cape Cod National Seashore.
Opens in a new windowBeau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Mid-Cape Cod Luxury Escape!!

Mid-Cape Cod Luxury Escape!!

Yarmouth MA
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 10-minute drive of Main Street Hyannis and Cape Cod Beaches.
Opens in a new windowMid-Cape Cod Luxury Escape!!
Save an average of 15% on thousands of hotels when you're signed in
Waterfront Cottage - fantastic unobstructed views!!

Waterfront Cottage - fantastic unobstructed views!!

Wellfleet MA
When you stay at this vacation home in Wellfleet, you'll be on the beach, within a 15-minute walk of Cape Cod Beaches and Cape Cod National Seashore.
Opens in a new windowWaterfront Cottage - fantastic unobstructed views!!
LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,SUNSET VIEWS,AC,2BR w/LOFT,KAYAK

LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,SUNSET VIEWS,AC,2BR w/LOFT,KAYAK

North Truro MA
The price is AU$1,317 per night from 25 May to 26 May
AU$1,317
25 May - 26 May
includes taxes & fees
When you stay at this vacation home in North Truro, you'll be on the beach, within a 5-minute drive of Commercial Street and Cape Cod Beaches.
Opens in a new windowLUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,SUNSET VIEWS,AC,2BR w/LOFT,KAYAK
Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food

Yarmouth Port MA
When you stay at this vacation home in Yarmouth Port, you'll be by the sea, within a 10-minute drive of Main Street Hyannis and Mayflower Beach.
Opens in a new windowClose to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham MA
The price is AU$1,057 per night from 22 May to 23 May
AU$1,057
22 May - 23 May
includes taxes & fees
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 ...
Opens in a new windowSand Bar-Dog Friendly on Cooks Brook Beach
Darling Cape Cottage - Steps from Downtown Harwich Port

Darling Cape Cottage - Steps from Downtown Harwich Port

Harwich MA
This vacation home is in the heart of Harwich Port, within a 10-minute walk of Bank Street Beach and Cape Cod Beaches.
Opens in a new windowDarling Cape Cottage - Steps from Downtown Harwich Port
Updated Beach House Deck Outdoor Shower!

Updated Beach House Deck Outdoor Shower!

Chatham MA
When you stay at this vacation home in South Chatham, you'll be by the sea, within a 10-minute walk of Cape Cod Beaches and Forest Beach.
Opens in a new windowUpdated Beach House Deck Outdoor Shower!
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
2178 Holiday Homes
Lowest Price
AU$125
Highest Price
AU$1,317
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!, Mid-Cape Cod Luxury Escape!!, Waterfront Cottage - fantastic unobstructed views!!, LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,SUNSET VIEWS,AC,2BR w/LOFT,KAYAK, Close to Beaches, Bay Sunsets, Whale Watches, Cape Playhouse, Kid Fun, Fine Food, Sand Bar-Dog Friendly on Cooks Brook Beach, Darling Cape Cottage - Steps from Downtown Harwich Port, Updated Beach House Deck Outdoor Shower!

Top trending hotels in South Wellfleet

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$250 per night from 8 June to 9 June
AU$250
8 June - 9 June
includes taxes & fees
Located in Provincetown, Harbor Hotel Provincetown is on the waterfront, within a 5-minute drive of Race Point Beach and MacMillan Pier.
Opens in a new windowHarbor Hotel Provincetown
Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AU$762 per night from 20 May to 21 May
AU$762
20 May - 21 May
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
Dune Crest Hotel

Dune Crest Hotel

2.5 out of 5
535 Route 6 North Truro MA
Fully refundableReserve now, pay when you stay
The price is AU$125 per night from 17 May to 18 May
AU$125
17 May - 18 May
includes taxes & fees
With a stay at Dune Crest Hotel in North Truro, you'll be within a 15-minute walk of Cape Cod National Seashore and Cape Cod Beaches.
Opens in a new windowDune Crest Hotel
Save an average of 15% on thousands of hotels when you're signed in
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$246 per night from 17 May to 18 May
AU$246
17 May - 18 May
includes taxes & fees
When you stay at The Provincetown Inn in Provincetown, you'll be on the beach, just steps from Commercial Street and Cape Cod Beaches.
Opens in a new windowThe Provincetown Inn
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.

Top Picks

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.