Family-friendly holiday rentals in Wellfleet Harbor

Sunny Deck, Harbor View. Walk to OysterFest!

Classic little Cape cottage in an ideal location. Less than ten minute drive to amazing ponds and bayside or ocean beaches. Views of the harbor from the large sunny deck with attached outdoor shower. Ten minute walk into town along Duck Creek marsh & over scenic Uncle Tim’s Bridge. Visit the shops & galleries, have lunch or grab a drink at one of the many restaurants in town. Walk to the fish market and come home grill dinner on the deck. 15 minutes bike ride to the closest ocean beach.

Private Bay Beach and Sunset Views! Dog friendly.

The beauty of Cape Cod awaits in this meticulous cottage with water views. Access to a private bayside beach is just steps away, across from the driveway and down a short sandy path. Beach chairs and beach towels included. Ride or walk 1 mi away to a great bike trail, or to National Seashore beaches, shops and restaurants. Or, relax at the cottage with updated amenities, appliances, comfortable beds, and a wonderful outdoor space with deck, fire pit, outdoor shower, lawn games and a hammock!

Beautiful Creekside Apartment in Wellfleet Center

Unique romantic apartment overlooking Duck Creek. One large living space which includes kitchen, work area, dining and air conditioned living room with a spectacular view. Queen bedroom and full bath. Small outdoor sitting area with table and chairs to watch the tide role in and out. See the sky change color at sunset and if lucky, catch the moon rise. Access to this private apartment is up a spiral staircase. Close to all of Wellfleet's restaurants, art galleries, town center and the pier.

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.

Magical Writers Cabin + hot tub in Wellfleet Woods

Escape to our unique Writer’s Cabin in the peaceful woods of Wellfleet—a magical retreat that feels like you're staying in a treehouse! You'll be surrounded by nature yet just minutes' drive from stunning beaches, crystal-clear ponds, scenic trails, and a short stroll to charming Wellfleet harbor and quaint town center. Relax and unwind at our brand-new Magnolia Spa (opening in June), featuring a hot tub and sauna. On-site massage therapy begins in July—ask us about exclusive guest rates!

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.

The Breeze Overlooking Minister's Pond

The Breeze is a luxurious, romantic cottage by a serene freshwater pond, surrounded by vibrant gardens. Perfect for a peaceful getaway, enjoy kayaking, canoeing, and relaxing on the dock, or explore nearby trails and the Cape Cod Rail Trail with provided bikes. Unwind with evenings by the fire pit, refreshing outdoor showers, and a plush queen bed for ultimate comfort. This private oasis offers tranquility, natural beauty, and 5-star attention to detail for your perfect escape.

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)

A Cape Escape with Water Views from Every Room

Come enjoy our family vacation home! A beautiful, serene escape perched above the salt marsh - with lovely views from every room, and a huge 1,000 square foot outdoor deck. Sleeps 8 comfortably. A 10-minute drive to charming Wellfleet center, and just an 8-minute drive to ocean beaches. NOTE: BEDSHEETS, LINENS & BATH TOWELS ARE INCLUDED IN PRICE! This is our family ''getaway'' - a place of treasured memories. We hope it can be the same for you!

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

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.