House holiday rentals in Wellfleet Harbor

Wellfleet Home Above the Trees

PLEASE INQUIRE! Custom-crafted, owner-designed + built home, appointed w/ our modern + mid-century inspired esthetic, artwork + furnishings, and open, refreshing layout. Treehouse-like feel, with w/ spacious decks wrapping around South-facing sunny property, w/ beautiful sunsets every evening thru high wooded views over Conservation land. All within 15 minutes of Provincetown, + within 5-10 minutes of Wellfleet’s unparalleled Ocean + Bayside beaches, pristine kettleponds, Town Center + Harbor.

Private Cape Cottage + Peaceful Relaxing Property

1/2 acre lot, on a private road. Your personal oasis. Enjoy all the natural wonders that Wellfleet and the outer Cape have to offer. Super close to it all! Take a walk, bike, or 4 minute drive to beautiful Indian Neck bay beach and oyster grounds! The amazing ocean beaches are 8 minutes away by car or 18 minute bike ride. Walk through the woods to the gorgeous salt marsh at the Pilgrim Springs conservation area, just down the dirt road from the house. We are so glad to share our home with you!

New modern style Cape Cod escape

Beautifully furnished,fully renovated 3BD,2BT duplex in a Fantastic location. Spacious yard. At the end of a cul-de-sac. Within minutes of Beaches, Trails, Great Pond and Wiley Park. The open living space invites gatherings of family and friends. Modern bathrooms, fully equipped kitchen with new appliances. Great outdoor space, patio, big tables,grill, plenty of parking, A/C window units, W/D. Sleeps up to 6 people.Linens, towels, beach towels/chairs & an umbrella provided.Peaceful Cape Cod home

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

10 min walk to Beach - Amazing View & Huge Deck

Enjoy an incredible view of Duck Meadow Tidal Marsh from this cozy cottage. Only a 10 minute walk to Boat Meadow Landing, a great bayside beach. Sip your morning coffee on our huge deck while enjoying the view. The deck includes a retractable roof if you would prefer to sit in the shade. Only minutes from incredible restaurants & shops in Orleans. This home includes AC, office space w/ monitors & a natural gas fireplace. Near the Cape Cod Rail Trail, hiking trails and numerous beach options!

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

Wellfleet Woods Escape

Open kitchen + living + dining, w/ a wooden pitched ceiling and two sliders overlooking the deck, backyard +marsh. Functional kitchen with Farm sink, DW, cooking and pantry essentials. Two comfortable bedrooms with window AC's, new mattresses, and blackout curtains. Bathroom w/ tub/shower + plenty of towels for beach or house use. Outdoor shower is great in warmer months! Enjoy this quiet, tucked away Wellfleet spot with lots of walking trails and beautiful sunset views just down the road.

Chequessett "Hide-Away"

Chequessett Neck area - Contact owner for more reasonable than published off-season long term (more than 14 days) rates. Walk to Powers Landing bayside beach from this hilltop setting. Very private, spacious, comfortable and clean 2 bed 2 bath ranch style home. Outdoor shower, and private deck. Interior steps to Washer and dryer located in garage below. Highchair availabe on request. Conveniently situated - close to Wellfleet center, Harbor, Mayo beach, Great Island, Duck Harbor.

Rum Runner’s Shack @ Historic Downtown Wellfleet

Located in Wellfleet Center, enjoy this sublime 528 sq. foot cottage - only 10 minutes from beaches and ponds in any direction. Near Winslow's Tavern, Wellfleet Marketplace, Hatch's, Uncle Tim’s Bridge, Mac's Shack and Wicked Oyster. This 1925 bungalow is the perfect site for a couple or a family 2 adults/2 young children - NOT 4 adults due to septic. Linens, ac, cable provided. Parking for ONE vehicle. June - Sept =7 day minimum with Sunday check-in. No pets or 3rd party booking.

Nehemiahs Nest: Healing Cape Cod Pond View Cottage

18+ Lovely waterfront tranquil getaway. All nearby houses hidden! This gem of a spot has been curated to soothe the soul! The cottage is sitting on Bakers Pond with an unobstructed view surrounded by conservation land *The driveway abuts a road* Wildlife can be observed. Swim or fish in this very clean kettle pond! The edges of the pond require water shoes for comfort as this is a natural body of water with no man-made beach/interference of nature. Kayaks, and life jackets available

Cove Road House

Bright and sunny Cape style house in beautiful Wellfleet. Located on a hill this house is private and cozy. A short drive to Wellfleet center, ocean beaches and ponds. Please note that linens are not included in your rental for weeklong summer stays. Parking for one large or 2 small cars is available at top of driveway and additional parking spaces at the lower part of driveway.

The Old Knotty - Walk to Bayside Beaches

‘The Old Knotty’ – tucked among the salty pine trees of Wellfleet’s Indian Neck, is a renovated 1950s knotty-pine cottage that blends classic Cape Cod charm with modern comfort. ▪️8-minute walk to Hiawatha Beach ▪️13 min bike ride or 6 min drive to downtown ▪️Dog-friendly (case-by-case, see below)