
Holiday houses in Wellfleet Harbor
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Top-rated holiday rentals in Wellfleet Harbor
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Writer’s Cabin • On-Site Hot Tub & Wood-fire Sauna
Our beloved “piece of heaven on earth” is a cabin-style tiny home filled with books—perfect for writers or a relaxing beach getaway. Perched on a gentle incline, the Writer’s Retreat feels private and tucked away among the trees. Just minutes’ drive from beaches and a short stroll to the charming center of Wellfleet. Unwind at our on-site SeaRose Spa, w/ a hot tub, saunas, & massage therapy (special guest rates) — part of our BnB property, which also includes two guest suites in the main house.
4.98 out of 5 average rating, 389 reviews
Spacious beautiful fully renovated Cape Cod escape
Beautifully furnished,fully renovated 4BD, 3BT duplex in 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. Cape Cod escape.Modern bathrooms, fully equipped kitchen with new appliances. Great outdoor space, patio, big tables- inside and outside, grill, plenty of parking, A/C window units, W/D. Sleeps up to 10. Linens, beach towels/chairs & an umbrella provided.
4.99 out of 5 average rating, 111 reviews
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.
4.92 out of 5 average rating, 214 reviews
Abundant Blessings Cottage – Wellfleet
Couple/family fun all year in a charming, private Cape Cod cottage w/ screened in porch, patio & outdoor shower (in Nov/Dec/Jan becomes a Gingerbread cottage). Inside: open living space w/ queen bed & sitting space. Ladder leads to a short height sleeping loft w/ 2 twin beds. Full bathroom w/ indoor shower. Kitchenette- see description below. We supply tea, local coffee, spices, condiments, gas grill, ice chests, beach towels & chairs. To sleep up to 8, also rent our Upper Room on Airbnb.
4.97 out of 5 average rating, 204 reviews
Cape Cod Spectacular Waterfront Cottage
Welcome to our internationally acclaimed and regionally featured cottage located on Lieutenant Island in Wellfleet, MA. It's in a private location with panoramic views and a western exposure featuring beautiful sunsets nightly (weather permitting)! TripAdvisor internationally featured property in July, 2015: Bostondotcom in July, 2016: Business Week in July, 2020. Please contact us for nightly, weekly or long term quotes or discounts. Pricing and lengths of stay are subject to change.
4.9 out of 5 average rating, 177 reviews
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.
4.93 out of 5 average rating, 105 reviews
RELAX! A Little of Heaven in Wellfleet
Indian Neck. Black Fish Creek. Shifting Tides. Private apartment. Spacious bedroom with king sized bed, living room with double bed. Kitchenette. Fully airconditioned. Views of the marsh. Outdoor shower. Private entrance into the ever-shifting Black Fish Creek salt marsh landscape full of fiddler and horseshoe crabs, fish, and seashore life. Easy 10 min walk along marsh or the road to two of Wellfleet’s most beautiful bay-side beaches—Omaha Beach and Field Point Beach.
4.97 out of 5 average rating, 68 reviews
Hillside Cottage
A one-bedroom cottage that sleeps 4, nestled into the hillside at the top of the wetland. Great for birding! Located on a beautifully landscaped property walking distance to Lecount Hollow Beach. The bedroom has a queen bed and there is a queen sleep sofa in the finished basement. There is also a studio apartment available on the premises that sleeps two. The listing name is "Comfortable Studio Apartment".(Pets are allowed in the studio appartment)
4.95 out of 5 average rating, 314 reviews
The Huddle Hut—a sweet, neat esCAPE to Wellfleet
The pristine Huddle Hut is nestled in a peaceful, wooded area only a short drive from beaches, restaurants, biking trails and Wellfleet's historic, charming town center. The Huddle Hut is perfect for couples and solo adventurers, only intended for one or two people at anytime: + nestled among trees in a quiet space + standalone building, private deck, outdoor shower + thoughtful, eclectic design + year-round getaway destination
4.99 out of 5 average rating, 193 reviews
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.
4.92 out of 5 average rating, 118 reviews
Classic Cottage with waterviews
Simple, classic cottage built c. 1907. 100 feet from the water in South Wellfleet on Blackfish Creek on Cape Cod Bay side. Waterviews from every bedroom. Low tide beachcombing and oyster activity, high tide swimming and sailing, boating or kayaking. Screened, wraparound porch with hammock. Air conditioned and heat but no insulation. Good mattresses. Herb garden.
4.9 out of 5 average rating, 102 reviews
The Perfect Cape Retreat
The perfect outer Cape retreat - cedar cottage nestled in the woods near a pond with a fireplace, vaulted ceilings, and 2 decks. 5 minutes to beaches, rail trail, and downtown. Cottage has wifi and a Smart TV. You won't want to leave! Need two houses in the same area? Search for our other cottage by Googling "The Perfect Getaway in Wellfleet".
4.95 out of 5 average rating, 217 reviewsPopular amenities for Wellfleet Harbor holiday rentals
Other great holiday rentals in Wellfleet Harbor

Sandy beach cottage on Wellfleet Bay
4.94 out of 5 average rating, 16 reviews
Lt Lodge~ Waterfront/King Bed/Dog-Friendly
4.87 out of 5 average rating, 38 reviews
10 min walk to Beach - Amazing View & Huge Deck
5.0 out of 5 average rating, 21 reviews
Wellfleet~Beautiful One Day Perfect The Next
4.87 out of 5 average rating, 67 reviews
Private Cape Cottage + Peaceful Relaxing Property
4.96 out of 5 average rating, 53 reviews
Wellfleet Cottage near Scenic Pond
4.75 out of 5 average rating, 121 reviews
The Chatham Bars White Foam House Steps From Beach
5.0 out of 5 average rating, 29 reviews
Beach house 9 minutes from PTown
5.0 out of 5 average rating, 6 reviewsDestinations to explore
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- Craigville Beach
- Onset Beach
- East Sandwich Beach
- Duxbury Beach
- Sandy Neck Beach
- Saquish Beach
- Nauset Beach
- New Silver Beach
- Skaket Beach
- Popponesset Peninsula
- Cape Cod Canal
- Falmouth Heights Beach
- Pinehills Golf Club
- Race Point Beach
- Inkwell Beach
- Coast Guard Beach
- Cape Cod Inflatable Park
- Cahoon Hollow Beach
- Nickerson State Park
- Sea Gull Beach
- Marconi Beach





