Book Holiday Homes in South Wellfleet

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Featured Holiday Homes in South Wellfleet

Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
A stay at this vacation home places you in the heart of Chatham, within a 5-minute walk of Mayo House and Gallery Antonia.
Opens in a new windowDowntown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Renovated cottage 1 mile to beach in Chatham!

Renovated cottage 1 mile to beach in Chatham!

Chatham
With a stay at this vacation home in Chatham, you'll be within a 5-minute drive of Chatham Chamber of Commerce and Veterans Field.
Opens in a new windowRenovated cottage 1 mile to beach in Chatham!

HARWICH PORT SPECIAL PLACE inquire about long-term

HARWICH PORT SPECIAL PLACE inquire about long-term

Harwichport
A stay at this vacation home places you in the heart of Harwich Port, within a 5-minute drive of Harwich Port and Bank Street Beach.
Opens in a new window HARWICH PORT SPECIAL PLACE inquire about long-term
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LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK

LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK

North Truro
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 National Seashore.
Opens in a new windowLUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK
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
With a stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Mayflower Beach and Cape Cod Theatre Company – Home of the ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Charming Home Close to Everything. AC splits  Jan-April monthly rate discounts

Charming Home Close to Everything. AC splits Jan-April monthly rate discounts

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Cape Cod National Seashore and Poit's Lighthouse Mini Golf.
Opens in a new windowCharming Home Close to Everything. AC splits Jan-April monthly rate discounts
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham
The price is AU$780 per night from 23 Oct to 24 Oct
AU$780
23 Oct - 24 Oct
includes taxes & fees
A stay at this vacation home places you in the heart of Chatham, within a 5-minute walk of Chatham Windmill and Mayo House.
Opens in a new windowQuaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail

Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Cape Cod National Seashore and Poit's Lighthouse Mini Golf.
Opens in a new windowCape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail
Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail

Chatham
With a stay at this vacation home in Chatham, you'll be within a 5-minute drive of Caleb Nickerson House and Chatham Marconi Maritime Center.
Opens in a new windowBeautiful home near Jacknife Beach and bike trail
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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.

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
2310 Holiday Homes
Lowest Price
AU$172
Highest Price
AU$780
Popular accommodation
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Renovated cottage 1 mile to beach in Chatham!, HARWICH PORT SPECIAL PLACE inquire about long-term , LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Charming Home Close to Everything. AC splits Jan-April monthly rate discounts , Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, Cape Getaway -walk to restaurants & shops, near bay & ocean beaches & rail trail, Beautiful home near Jacknife Beach and bike trail

Top trending hotels in South Wellfleet

Sandcastle Resort and Club

Sandcastle Resort and Club

3 out of 5
929 Commercial Street, Provincetown, MA
The price is AU$172 per night from 30 Sept to 1 Oct
AU$172
30 Sept - 1 Oct
includes taxes & fees
Located in Provincetown, Sandcastle Resort and Club is by the ocean, within a 5-minute drive of Race Point Beach and Cape Cod National Seashore.
Opens in a new windowSandcastle Resort and Club
Captains Quarters Motel & Conference Center

Captains Quarters Motel & Conference Center

2 out of 5
5000 State Highway/Route 6, Eastham, MA
Fully refundableReserve now, pay when you stay
With a stay at Captains Quarters Motel & Conference Center in Eastham, you'll be near the beach, within a 5-minute drive of Cape Cod National Seashore and Poit's ...
Opens in a new windowCaptains Quarters Motel & Conference Center
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$290 per night from 22 Oct to 23 Oct
AU$290
22 Oct - 23 Oct
includes taxes & fees
When you stay at The Provincetown Inn in Provincetown, you'll be on the beach, a 1-minute drive from Commercial Street and 6 minutes from Cape Cod National ...
Opens in a new windowThe Provincetown Inn
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The Villages at Ocean Edge

The Villages at Ocean Edge

3.5 out of 5
One Villages Drive, Brewster, MA
The price is AU$249 per night from 26 Oct to 27 Oct
AU$249
26 Oct - 27 Oct
includes taxes & fees
Located in Brewster, The Villages at Ocean Edge is a 4-minute drive from Breakwater Beach and 6 minutes from Cape Cod Museum of Natural History.
Opens in a new windowThe Villages at Ocean Edge
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See all available properties in South Wellfleet
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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.