South Wellfleet, MA Vacation Homes from ￥66,070

South Wellfleet Vacation Homes
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Our top choices for South Wellfleet vacation homes

A cozy cabin interior with a wooden interior, a dining area, a sofa, and a staircase.

A wooden cabin with a glass door leading to a dining area with a table and chairs.

A wooden outdoor shower area with a metal faucet, surrounded by wooden beams and walls.

A cozy cabin interior with a wooden dining area, a sofa, and a small table with a lamp.

1. New! Island Pines-A Dog Friendly Boutique Oasis

New! Island Pines-A Dog Friendly Boutique Oasis

Wellfleet

9.4 out of 10, Exceptional, (12 reviews)

9.4/10

Exceptional

(12 reviews)

"Beautiful cozy home on a piney coastal island! Wish we could stay longer. Very central for exploring in all directions on the Cape. Awesome hosts with so many great recommendations and thorough info leading up to the stay."

Kaden P.

The price is ￥36,187

￥36,187

￥97,431 total

includes taxes & fees

Oct 13 - Oct 14

New! Island Pines-A Dog Friendly Boutique Oasis

A cozy room with a bed, two chairs, a ceiling fan, and two windows with curtains.

A cozy living room with wicker furniture, a painting of sailboats, and a ceiling fan.

A wooden deck with metal chairs overlooking a beach with clear turquoise water and a cloudy sky.

2. Waterfront~Dog Friendly~ Lieutenant's Lodge

Waterfront~Dog Friendly~ Lieutenant's Lodge

Wellfleet

9.8 out of 10, Exceptional, (15 reviews)

9.8/10

Exceptional

(15 reviews)

"My family of 6 (with 4 kids ranging from 5 to 16) all loved it here! We hope to stay again in the future! Super comfortable beds!"

Lorie D.

The price is ￥41,367

￥41,367

￥107,876 total

includes taxes & fees

Oct 4 - Oct 5

Waterfront~Dog Friendly~ Lieutenant's Lodge

A dining table with wine glasses, plates, and a bottle, set against a window with a view of trees and a paddleboard.

A river flowing through a rocky landscape with a wooden viewing platform.

A cozy living room with a sectional sofa, a coffee table, and a large window with a view of trees.

A hotel room with two beds, a dresser, a mirror, a window with a view of greenery, and a beach-themed wall art.

3. 🐚Shell City on Lt Island

🐚Shell City on Lt Island

Wellfleet

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 reviews)

"We had a perfect three night stay. The house is well appointed with comfortable beds, sheets, and towels. We used the bikes and kayaks and everything was in working order. We would gladly stay again!"

Michele P.

The price is ￥39,634

￥39,634

￥112,544 total

includes taxes & fees

Oct 13 - Oct 14

🐚Shell City on Lt Island

An outdoor deck with a grill, dining table, chairs, and an umbrella.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

A wooden house with blue shutters, a front door, and a small porch with steps.

A dining table set with plates, glasses, and a vase of flowers, with chairs around it.

4. Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Eastham

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"We went with a small group of friends and everything was amazing. The property is beautiful and well located. We had everything that we needed and the communication con the owner was good."

Lourdes P.

The price is ￥24,469

￥24,469

￥82,038 total

includes taxes & fees

Oct 13 - Oct 14

Sleeps 2-8/Soaking Tub/FirePit~Burrows

A beach with a wooden fence and a clear view of the ocean.

A cozy room with wooden paneling, a large bed with white linens, two bedside lamps, and a small bedside table.

A residential driveway with a wooden fence and trees.

A kitchen with granite countertops, white cabinets, and a dining area with a table set for two.

5. The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!

Eastham

9.2 out of 10, Wonderful, (12 reviews)

9.2/10

Wonderful

(12 reviews)

"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."

Jennifer G.

The price is ￥24,987

￥24,987

￥82,630 total

includes taxes & fees

Oct 13 - Oct 14

The Alpine/Walk to Beach for 2 or more!

A dining table set with plates, glasses, and a variety of food including grapes, cheese, and crackers.

A spacious living room with a high ceiling, skylights, a large sofa set, a coffee table, and a flat-screen TV mounted on the wall.

A wooden corridor leading to a room with a window, a towel hanging on the wall, and a basket with pink towels.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area set with a dark wooden table, woven placemats, and a variety of food and drinks.

6. National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl

Eastham

10.0 out of 10, Exceptional, (9 reviews)

10/10

Exceptional

(9 reviews)

"We had an wonderful experience staying at this house. It was exceptionally clean and it had everything we needed (it was nice to have linens and towels provided). All of the rooms were relaxing and comfortable and the kitchen was very well equipped. I would definitely stay there again. "

Catharine D.

The price is ￥23,959

￥23,959

￥74,621 total

includes taxes & fees

Oct 1 - Oct 2

National Seashore/Updated/Game Room~Blue Pearl

A wooden outdoor shed with a door, a window, and a gravel path leading to it.

A wooden chair with a cushion on a balcony with a view of a building and a window.

A living room with a fireplace, a ceiling fan, and a dining area with a table and chairs.

A kitchen with wooden cabinets, a blue countertop, and a breakfast setup including bowls, mugs, and a cereal box.

7. Gray Whale-Minutes to Eastham Bay & Ocean Beaches

Gray Whale-Minutes to Eastham Bay & Ocean Beaches

Eastham

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"very well appointed accommodations - great location - helpful amenities. would come back again!"

Leonard

The price is ￥30,673

￥30,673

￥90,038 total

includes taxes & fees

Oct 13 - Oct 14

Gray Whale-Minutes to Eastham Bay & Ocean Beaches

A dining area with a wooden table set for four, surrounded by chairs. A large mirror hangs on the wall, reflecting the room.

A cozy living room with a wooden floor, two sofas, a rocking chair, a fireplace, and a framed picture on the wall.

A kitchen with a sink, cabinets, and a window. There is a dining table with chairs.

A cozy room with a wooden table, a lamp, and a book titled "Cape Cod" on a chair.

8. Ebb Tide~3b/2b and dog friendly for 2-10

Ebb Tide~3b/2b and dog friendly for 2-10

Wellfleet

8.8 out of 10, Excellent, (5 reviews)

8.8/10

Excellent

(5 reviews)

"Great stay. Kind extra touches of hospitality appreciated!"

Ross M.

The price is ￥26,372

￥26,372

￥88,552 total

includes taxes & fees

Oct 1 - Oct 2

Ebb Tide~3b/2b and dog friendly for 2-10

A sandy beach with wooden posts and a clear view of the ocean.

A cozy living room with a brick fireplace, a wooden coffee table, and a bookshelf.

A hotel room with a large bed, a bedside table with a lamp, a chair, and a window with curtains.

A table set with bowls, glasses, and bottles of Grinno mineral water.

9. Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham

10.0 out of 10, Exceptional, (33 reviews)

10/10

Exceptional

(33 reviews)

"We had a lovely visit with access to the beach and very comfortable beds. Enjoyed a beautiful sunset!"

Debra H.

The price is ￥31,199

￥31,199

￥84,530 total

includes taxes & fees

Oct 1 - Oct 2

Sand Bar-Dog Friendly on Cooks Brook Beach

A patio with Adirondack chairs, a fire pit, and a wooden deck.

A neatly made bed with white linens, a remote control, a small gift bag, and a decorative item on a blue woven placemat.

A dining table with plates, cutlery, and a bottle, surrounded by white chairs.

A living room with a grey sofa, a wooden coffee table, and a dining area with chairs and a table.

10. Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Eastham

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"The house was cute and clean. The private beach was amazing. We enjoyed our stay!"

Susan W.

The price is ￥23,264

￥23,264

￥66,070 total

includes taxes & fees

Oct 13 - Oct 14

Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

A staircase with a wooden handrail and a red carpet leading to a room with a chair and a framed picture on the wall.

A room with a blue door, a white sink, and a small rug.

A deck with blue chairs and a small table, surrounded by a white railing.

11. 2 Bedroom Private Apt. in 1825 Whaler's Home on Duck Creek

2 Bedroom Private Apt. in 1825 Whaler's Home on Duck Creek

Wellfleet

8.4 out of 10, Very good, (8 reviews)

8.4/10

Very good

(8 reviews)

"Lighting was poor in the communal space. , mattresses lumpy but okay. The couch in the communal space very low for a senior person. "

Miriam H.

The price is ￥38,949

￥38,949

￥83,302 total

includes taxes & fees

Oct 1 - Oct 2

2 Bedroom Private Apt. in 1825 Whaler's Home on Duck Creek

A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

A cozy living room with a fireplace, two sofas, a coffee table, and a bookshelf.

A neatly made bed with striped pillows and a plain white comforter.

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

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

Eastham

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"

Kim S.

The price is ￥24,469

￥24,469

￥82,038 total

includes taxes & fees

Oct 13 - Oct 14

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

A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

A spacious bedroom with a large bed, a bench, a desk, and a chair. There are multiple windows and a door.

A living room with a sofa, a coffee table with magazines, a bookshelf, and a kitchen in the background.

A two-story house with a stone retaining wall, large windows, and a deck.

13. Pond House~Waterfront Oasis on Minister's Pond

Pond House~Waterfront Oasis on Minister's Pond

Eastham

10.0 out of 10, Exceptional, (13 reviews)

10/10

Exceptional

(13 reviews)

"Had everything we needed for a comfortable stay."

BILL

The price is ￥24,649

￥24,649

￥82,258 total

includes taxes & fees

Oct 4 - Oct 5

Pond House~Waterfront Oasis on Minister's Pond

Living room with plenty of seating and beautiful coastal design

A single-story house with a front porch, a chimney, and a small front yard with shrubs.

A cozy living room with a brick fireplace, a lamp, and a blue patterned armchair with a cushion labeled "Awind".

A bedroom with a large bed, a ceiling fan, a small seating area, and a window.

14. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Eastham

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Our family enjoyed the downstairs activities, especially nice for the kids to play and adults upstairs. All the bedrooms/baths clean and very nice. Loved our stay. "

Donna R.

The price is ￥30,157

￥30,157

￥104,217 total

includes taxes & fees

Oct 13 - Oct 14

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

A wooden interior with a wooden ceiling, a sliding glass door leading to a living area, and a blue cushioned chair.

An aerial view of a beachside parking lot adjacent to a sandy beach with a clear view of the ocean.

A harbor with a white boat docked at a pier, a lighthouse in the background, and a row of houses along the shore.

15. Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"Great house with comfy beds. Would consider staying again. "

Susan C.

The price is ￥23,454

￥23,454

￥76,517 total

includes taxes & fees

Oct 19 - Oct 20

Lovely House 5 Min to Beach with Deck, Grill, Garage

A wooden table set outdoors with plates, glasses, a bottle, and a metal container.

A spacious living area with a large sectional sofa, a dining table, and a kitchen in the background.

A modern kitchen with white cabinetry, a central island with a black placemat, and two white chairs.

A wooden exterior with a metal door and a towel hanging on a hook.

16. Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Eastham

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Driftmoor was a fantastic place to stay for our Labor Day trip to Provincetown. The property is extremely clean and spacious. The location was convenient to several local eateries. Management was easy to communicate with."

David

The price is ￥29,123

￥29,123

￥88,083 total

includes taxes & fees

Oct 13 - Oct 14

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

A living room with a grey sofa, striped rug, and a lamp.

A house with a white porch, a door, and a garden with flowers and greenery.

A spacious living room with a large gray sectional sofa, a wooden coffee table, and a view of the kitchen through an open door.

A modern kitchen with white cabinets, a stainless steel stove, and a refrigerator.

17. The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham

10.0 out of 10, Exceptional, (28 reviews)

10/10

Exceptional

(28 reviews)

"Our host was very responsive and all the instructions were clear. The house was immaculate and a perfect spot of a winter getaway. Would stay again!"

Anna P.

The price is ￥24,131

￥24,131

￥74,819 total

includes taxes & fees

Oct 5 - Oct 6

The Pet-Friendly Surf Shack Hideaway on the Cove

A table set for two with a view of the sunset over the water, outdoor seating, and a grill area.

A corner room with a telescope on a tripod, two chairs, a table with a patterned tablecloth, and a view of the beach.

A wooden boardwalk leading to a beach with a clear view of the ocean.

A bedroom with a large bed, two windows with a sunset view, a chair, and a bedside table with a lamp.

18. Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Eastham

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Just perfect all around!"

Alexis N.

The price is ￥37,231

￥37,231

￥80,265 total

includes taxes & fees

Oct 8 - Oct 9

Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

A deck with outdoor seating and a view of the ocean at sunset.

A living room with a sofa and armchairs, large windows with a view of the sunset over the water, and a side table with a lamp.

A wooden staircase leading to a beach with a wooden boardwalk and lush greenery.

A beach house with a staircase leading to a sandy area, surrounded by large rocks and greenery.

19. Beachfront~Seaside Sea-duction-Dog Friendly

Beachfront~Seaside Sea-duction-Dog Friendly

Eastham

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"Great place. Beautiful mornings, days, and evenings. "

Keith B.

The price is ￥54,626

￥54,626

￥123,938 total

includes taxes & fees

Oct 13 - Oct 14

Beachfront~Seaside Sea-duction-Dog Friendly

A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

A wooden interior with a large dining table, potted plants, and a view of the landscape through large windows.

A wooden deck with potted plants, a wooden door, and a view through a window.

A row of white buildings with storefronts, including a visible sign for 'The Chatham Inn.'

20. 10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

The price is ￥39,195

￥39,195

￥95,867 total

includes taxes & fees

Oct 27 - Oct 28

10 min walk to Beach - Home with Amazing View & Huge Deck

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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