Family-friendly holiday rentals in Wellfleet

4.98 out of 5 average rating, 389 reviews

Tiny home in Wellfleet

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.

An open living space showcases a comfortable blue sofa and a large wooden dining table. Natural light floods the area through sliding doors, leading to an outdoor patio. Neutral tones and wooden accents create a cohesive and inviting environment for relaxation and gatherings.

4.99 out of 5 average rating, 111 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.

The kitchen area features a wooden pitched ceiling and a functional layout. A farmhouse sink is paired with stainless steel appliances and cooking essentials. Two stools are positioned at a counter, with a small vase of flowers adding a touch of nature. Glass doors offer views to an outdoor deck.

4.92 out of 5 average rating, 214 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.

4.97 out of 5 average rating, 204 reviews

A charming cottage is surrounded by a grassy yard, featuring a set of four blue Adirondack chairs arranged around a small glass table. A gas grill is situated nearby, and a tree provides dappled shade to the area.

Guesthouse in Wellfleet

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.

A ranch-style home is nestled among tall trees, featuring a sloped roof and wood shingle siding. A small front porch is positioned beside the entrance, with a pathway leading to the door. Air conditioning unit is visible on the side of the house.

4.93 out of 5 average rating, 105 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.

An outdoor deck extends over panoramic views of the waterfront, featuring a dining table with dark wood chairs shaded by a green umbrella. The deck is surrounded by lush greenery and offers ample space for relaxation and dining, enhancing the outdoor experience.

4.9 out of 5 average rating, 177 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.

A cozy living area features a blue sofa adorned with yellow decorative pillows, positioned in front of a wooden coffee table. Natural light enters through large windows, illuminating the space. A wooden ladder leads to a loft area, complemented by a light rug underfoot.

4.92 out of 5 average rating, 143 reviews

Cozy 3 bedroom cottage in the Heart of Wellfleet

Escape to the Cape and enjoy the National Seashore! Wellfleet is home to some of Cape Cod's finest beaches, art galleries, shops, restaurants, and of course, the oysters. Our cottages is tucked away yet is within walking distance to Power's Landing beach, Mayo Beach, and the Pier. Wellfleet has so much to offer and we'd love to be able to help make your stay all the more memorable. Our quaint home offers all the modern necessities you want yet keeping the cottage vibe.

A charming cottage features a welcoming front porch with steps leading to a white railing. The exterior showcases cedar shingles and large windows that invite natural light. Lush greenery surrounds the home, complemented by flowering trees that enhance the peaceful environment.

4.99 out of 5 average rating, 205 reviews

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. Linens, ac, cable provided. Parking for ONE vehicle. June - Sept =7 day minimum with Sunday check-in. No pets or 3rd party booking.

A charming cottage is nestled on a hillside, surrounded by lush greenery. The exterior features a light wood facade and a welcoming front porch with seating. The landscaped yard is manicured, offering a natural setting that blends harmoniously with the surrounding environment.

4.95 out of 5 average rating, 316 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)

4.98 out of 5 average rating, 118 reviews

Row of charming cottages lined along a sandy beach, with white lounge chairs positioned for relaxation. The tranquil bay is visible in the foreground, while the skyline is seen in the distance, under a bright blue sky dotted with soft clouds.

Cottage in Truro

Private Beachfront, AC, EV, Kayaks, Renovated!

10% off Weeklong Off-Season bookings! Welcome to Larkspur Cottage, part of the "Days' Cottages," one of the 22 white and teal cottages located right before Provincetown, complete with its own private beach, portable AC unit and convenient located next door to an EV charging station! Enjoy majestic views and romantic sunsets. This newly updated cottage is carefully decorated to ensure a comfortable, relaxing, and memorable stay.

A Cape style house is nestled among greenery, surrounded by tall trees and bushes. Windows are framed by natural foliage, providing a sense of privacy. The front yard features potted plants, contributing to a cozy, inviting exterior. The building showcases a sloped roof and a classic shingled facade.

4.92 out of 5 average rating, 119 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.

4.9 out of 5 average rating, 134 reviews

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.

Popular amenities for Wellfleet family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 322 reviews

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

Home in Chatham

Slate House - a modern waterfront getaway

4.96 out of 5 average rating, 169 reviews

Two kayaks are stored beside a shed in a natural setting, surrounded by tall grass. A view of the calm water reflects the greenery of the area, while a cozy indoor space showcases a gas fireplace and comfortable furnishings.

Cottage in South Dennis

Local Beach+ Fireplace + Hot Tub Under the *Stars*

5.0 out of 5 average rating, 105 reviews

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Condo in Brewster

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

4.92 out of 5 average rating, 319 reviews

The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.

Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

4.96 out of 5 average rating, 240 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

Lakefront House/Private Dock/Year Round Hot Tub/AC

4.83 out of 5 average rating, 105 reviews

The beachfront property is showcased against a vibrant sunset sky, with gentle waves lapping the sandy shore. Steps built into the rocky landscape lead down to the beach, while coastal homes are visible in the background, creating a serene and inviting setting.

Home in Dennis Port

Gorgeous Modern Ocean-Front Cottage With Hot Tub

Superhost

The exterior of the property is illuminated by warm string lights, creating a welcoming ambiance. A large deck is visible, featuring a railing that leads to a well-maintained lawn, while the 'Cape Cod' neon sign adds a playful touch to the scene.

Home in East Dennis

Bayside Oasis with Hot Tub & Game Room

4.92 out of 5 average rating, 111 reviews

4.97 out of 5 average rating, 127 reviews

A covered outdoor seating area features a comfortable sectional sofa with neutral cushions and a round coffee table. A dining table with several chairs is positioned nearby, alongside an outdoor kitchen equipped with a grill. Sunlight casts distinct shadows across the space.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

Family- and pet-friendly home rentals

A charming outdoor deck area features a large picnic table surrounded by lush greenery and colorful flower beds. Two comfortable chairs are positioned nearby, with an umbrella providing shade. The sunny, serene setting is complemented by a clear blue sky in the background.

4.99 out of 5 average rating, 123 reviews

Large Sunny Deck, Harbor View, Walk to Town.

4.91 out of 5 average rating, 279 reviews

A cozy living area is presented with light-colored walls and wooden floors. Comfortable seating includes two upholstered chairs and a sofa with a neutral cover. A coffee table sits in front, and the open kitchen is visible in the background, enhancing the space's inviting nature.

Home in Truro

Cape Cod Getaway 2 Bedroom Cozy Home

4.96 out of 5 average rating, 209 reviews

A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

Home in Eastham

The Sea Captain's Carriage House

A charming, light-colored house sits under a clear sky, surrounded by trees. The front entry features a welcoming pathway, two white Adirondack chairs, and a small table with flower pots. Large windows provide views into the interior, while a well-maintained garden enhances the curb appeal.

4.86 out of 5 average rating, 135 reviews

Walk to Beach, Pet Friendly, New Fenced Backyard!

4.93 out of 5 average rating, 129 reviews

The exterior of a charming cottage is displayed, featuring a brick chimney and light-colored shingles. Lush greenery surrounds the property, complemented by two blue planters near the entrance. A stone pathway leads to the door, and a picnic table is visible on the adjacent patio.

Cottage in Truro

Unique Waterfront Artist Cottage

4.93 out of 5 average rating, 187 reviews

A studio cabin is positioned on a gently sloping green lawn, surrounded by trees. The porch extends from the cabin, featuring blue seating. A vehicle is visible on the driveway, complementing the serene natural setting.

Guesthouse in Wellfleet

Cabin @ Newcomb Hollow Beach

A rustic cottage is seen with a light-colored exterior and a shingled detailing. The porch features a small table surrounded by four chairs, while two lounge chairs sit nearby. Large windows allow natural light to enter, framed by a backdrop of trees.

4.99 out of 5 average rating, 73 reviews

Wellfleet Cottage By The Sea

5.0 out of 5 average rating, 27 reviews

Charming, Cozy Main-St Cottage

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 264 reviews

A scenic view showcasing the bay with gently rippling waters and distant land on the horizon. The foreground features coastal vegetation, including pines and shrubs, along a wooden pathway leading toward the beach. Nearby, a stop sign indicates road access.

Condo in Provincetown

P-Town Beach Beauty on the Bay. Water View!

4.89 out of 5 average rating, 179 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

4.87 out of 5 average rating, 125 reviews

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

Ocean Edge Cape House with Beach, Pool, and AC

4.97 out of 5 average rating, 183 reviews

Condo in New Seabury

New Seabury Cape Condo | Pool & Beach Escape

A charming cottage exterior is showcased, featuring natural wood shingles and red shutters. A bright orange door provides a welcoming entrance. Lush green leaves frame the image, highlighting the serene surroundings of the property against a clear sky.

4.87 out of 5 average rating, 67 reviews

Wellfleet~Beautiful One Day Perfect The Next

An expansive in-ground heated saltwater pool is surrounded by a spacious patio. A gazebo is situated nearby, framed by lush trees. Lounge chairs with umbrellas provide shaded seating, while a hammock offers a relaxing spot. The pool reflects the clear blue sky, creating a serene outdoor setting.

5.0 out of 5 average rating, 15 reviews

Lovely villa w pool/hottub, central AC, near beach

5.0 out of 5 average rating, 12 reviews

Game Room- Movie Projector Room- Fire Pit

Superhost

A distinctive A-frame cottage is situated among tall trees, surrounded by natural greenery. The entrance features a wooden deck with a picnic table and two chairs, inviting relaxation in the outdoors. Clear skies provide ample sunlight, enhancing the cottage's inviting atmosphere.