Book Holiday Homes in South Wellfleet

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Featured Holiday Homes in South Wellfleet

Your Perfect Home-Away-From Home in the Heart of Provincetown.

Your Perfect Home-Away-From Home in the Heart of Provincetown.

Provincetown
When you a stay at this vacation home in Provincetown, you'll be by the sea, just steps from Provincetown Public Library and Commercial Street.
Opens in a new windowYour Perfect Home-Away-From Home in the Heart of Provincetown.
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
The price is AU$483 per night from 14 Nov to 15 Nov
AU$483
14 Nov - 15 Nov
includes taxes & fees
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
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2 out of 5
Brewster
The price is AU$995 per night from 18 Nov to 19 Nov
AU$995
18 Nov - 19 Nov
includes taxes & fees
With a stay at this vacation home in Brewster (West Brewster), you'll be a 2-minute drive from Sheep Pond and 6 minutes from Breakwater Beach.
Opens in a new windowCoastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
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Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

2 out of 5
Yarmouth
Located in South Yarmouth, this vacation home is within a 5-minute drive of Bass River Sports World and Captain Bangs Hallett House.
Opens in a new windowMid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard
Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Chatham
When you stay at this vacation home in West Chatham, you'll be by the sea, within a 10-minute walk of Ridgevale Beach and Cape Cod Beaches.
Opens in a new windowSpacious, private cottage just a few minutes walk to Ridgevale Beach!
Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, just a 2-minute walk from Cape Cod Beaches and 7 minutes by foot from Campground Beach.
Opens in a new windowSteps to a private bay beach from this private & Charming Cape! Book this Fall!
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 Chatham Windmill.
Opens in a new windowDowntown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
Located in Chatham, this vacation home is by the sea, within a 5-minute drive of Hardings Beach and Cape Cod Beaches.
Opens in a new windowBreathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Ocean view getaway with a deck & shared yard - walk to the beach

Ocean view getaway with a deck & shared yard - walk to the beach

Dennis Port
When you a stay at this vacation home in Dennis Port, you'll be on the beach, within a 5-minute walk of Cape Cod Beaches and Sea Street Beach.
Opens in a new windowOcean view getaway with a deck & shared yard - walk to the beach
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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$359
Highest Price
AU$995
Popular accommodation
Your Perfect Home-Away-From Home in the Heart of Provincetown., 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard, Spacious, private cottage just a few minutes walk to Ridgevale Beach!, Steps to a private bay beach from this private & Charming Cape! Book this Fall!, Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Ocean view getaway with a deck & shared yard - walk to the 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$625 per night from 14 Dec to 15 Dec
AU$625
14 Dec - 15 Dec
includes taxes & fees
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.
Opens in a new windowChatham Bars Inn
Wequassett Resort and Golf Club

Wequassett Resort and Golf Club

5 out of 5
2173 Head of the Bay Road, Route 28, Harwich, MA
When you stay at Wequassett Resort and Golf Club in Harwich, you'll be on the beach, within a 5-minute drive of Cape Cod Beaches and Caleb Nickerson House.
Opens in a new windowWequassett Resort and Golf Club
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
With a stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, just a 1-minute walk from Mayo House and 7 minutes by foot from Chatham ...
Opens in a new windowChatham Wayside Inn
Save an average of 15% on thousands of hotels when you're signed in
Surfside Hotel and Suites

Surfside Hotel and Suites

2.5 out of 5
543 Commercial Street, Provincetown, MA
The price is AU$359 per night from 15 Nov to 16 Nov
AU$359
15 Nov - 16 Nov
includes taxes & fees
With a stay at Surfside Hotel and Suites in Provincetown, you'll be on the beach, just steps from Cape Cod Beaches and a 3-minute drive from Provincetown Town ...
Opens in a new windowSurfside Hotel and Suites
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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.

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