Holiday rentals with outdoor seating in Wellfleet

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

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.

Large Sunny Deck, Harbor View, Walk to Town.

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.

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.

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.

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.

Cottage Getaway walk to beach

This Cute As Can Be Beach House is looking for guests! Just a five minute stroll to the beach, The Cottage is the perfect spot for a getaway. Open floor plan with spacious living-room, two bedrooms and bath. Large yard with outdoor shower and a hammock big enough for two! Includes beach chairs, towels, cooler. A true gem! Amenities -Air Conditioning -Heat -Smart TV -Wi-Fi -Gas grill/firepit -Two patios -Washer/Dryer -Outdoor shower - Parking -Adirondack chairs -Amazing sunsets

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.

Cape Cod Getaway 2 Bedroom Cozy Home

Newly updated in March 2023 with new white interior paint, new black doorknobs and cabinet pulls and new blinds throughout the home. Fresh paint, updated hardware, some new small appliances and added new art but same Cape cottage charm! NOTE: Weekly rentals mid-June through mid-September- Linens and towels can be provided in a basket or you are welcome to bring yours from home- just let us know. During this time (Mid June through Mid September, check in and out are on Saturdays.

3A Boulevard

Perfectly located creekside on Commercial Street halfway between Mac's Shack and the Pier. This flat in a centuries' old whale merchant's home on Duck Creek is perfect for active types who prefer to walk & bike. 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, Garden, Blockhouse, or Green Frog. Rent multiple apartments for larger parties.

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