Holiday houses in Wellfleet

Writer’s Cabin • On-Site Spa w/ Hot Tub & Massage

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.

In the Heart of Wellfleet and Walk to Mayo Beach

Beautifully renovated 1850 Greek revival house. Private apartment is on the second floor with private wide accessible outside stairway. It is a 3-4 room apartment and is perfect for a couple and at most a total of 4 adults. PLEASE NOTE if you are not a couple and do not want to share a bed , you will need to rent the second bedroom at $45 per night per each additional person.The location is perfect in the center of quaint picturesque downtown Wellfleet. Private parking. No children under 8.

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

2 Calypso

Welcome to Doub-Erickson House, the best location in Wellfleet. This fully self-contained flat in a 2 centuries old whale merchant's home on Duck Creek is perfect for active types who prefer to walk instead of drive. Ideal for kayakers & bikers. Steps from Wellfleet's best restaurants, town pier and the village center shopping & market. We have 5 flats. If one is booked on your dates, look for Calypso, Boulevard, Garden, Blockhouse, or Green Frog. Rent multiple apartments for larger parties.

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.

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.

The Wellfleet Beach House. Sleeps 6

On the road to Cape Cod's most loved beaches at the National Seashore. Come around the corner and pull into this property and you will instantly feel at home. This little gem is a three-bedroom Cape style with two bedrooms upstairs and a full bath with a walk-in shower. You will find another full bedroom and bath w/tub on the first floor. Open living/dining room & great kitchen. This property offers comfort and privacy with a level spacious backyard, firepit & outdoor shower.

Wellfleet Oasis

Unwind in this calm, stylish studio oasis. Stroll to Mass Audubon or bike just 1.3 miles along the trail next to our development to reach Marconi Beach. Enjoy local restaurants, a flea market, and Wellfleet Drive just 0.9 miles away. A small market on the Eastham-Wellfleet line offers essentials, sandwiches, and drinks. With owners on-site, the space features a private entrance, a deck with an electric grill, and an outdoor solar shower for rinsing off after a sunny day.

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 and a single 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)

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

Classic Summer Cottage

Stay at a classic summer cottage, in the Wellfleet woods, yet conveniently located a 5 minute drive from downtown Wellfleet. Built in 1938 by 4 women, it still has much of it's original charm. The great room has wood paneling and a cathedral ceiling. This common area has natural wood floors and a fireplace. 2 cozy bedrooms and a small kitchen and bathroom complete the scene.

Wellfleet Center Gem

Charming, pristine, top floor, 1-BR apartment with a sunny deck. Perfect for a couple or a solo traveler. Located in a historic building in the heart of Wellfleet Center. Great restaurants, shops, yoga/fitness, galleries, and farmers market are all steps from your door. Great option for those who love to walk. 20 minute drive to Provincetown. No pets allowed.