Vacation rentals with outdoor seating in Wellfleet

4.98 out of 5 average rating, 357 reviews

Tiny home 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.

4.98 out of 5 average rating, 112 reviews

A cozy living area is furnished with a comfortable sofa adorned with decorative pillows. A dining table with seating for four is visible, alongside a well-equipped kitchen in the background. Natural light enters through the windows, highlighting the warm wood floors.

Apartment in Wellfleet

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.

5 out of 5 average rating, 108 reviews

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.

Cottage in Wellfleet

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.

4.87 out of 5 average rating, 128 reviews

A spacious living area is visible, featuring a modern couch and stools at a kitchen bar. Light-colored wood floors are complemented by a decorative area rug. The kitchen includes various appliances, and artwork adorns the walls, adding character to the inviting space.

Apartment in Wellfleet

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.

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.

4.91 out of 5 average rating, 196 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, 194 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.

4.9 out of 5 average rating, 177 reviews

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.

Cottage in Wellfleet

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.

4.91 out of 5 average rating, 268 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

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.

4.98 out of 5 average rating, 55 reviews

Guesthouse in Wellfleet

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.

4.96 out of 5 average rating, 281 reviews

A prominent sign marks the entrance to Cape Cod National Seashore Salt Pond Visitor Center. Surrounded by greenery, the sign features bold lettering identifying the center and includes the National Park Service emblem, set against a backdrop of trees and a clear blue sky.

Apartment in Eastham

National Seashore Escape

There is no interaction required with hosts during stay. 1/4 mile to National Seashore Salt Pond Visitor Center and 2.0 miles to Coast Guard Beach, rated America's 6th best beach in 2019 by Dr Beach. The studio is above the garage with a private entrance private bath with shower. Queen bed, wifi, whisper quiet mini split a/c no window unit, tv. There is a kitchenette with refrigerator, microwave, coffee maker, toaster, sink, no stove.

4.99 out of 5 average rating, 181 reviews

The exterior of The Huddle Hut features a striking purple facade accented with light green trim. A welcoming entrance is highlighted by a gabled roof and a front porch. Bright floral planters add a touch of color, nestled beneath large windows that invite natural light.

Tiny home in Wellfleet

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

4.98 out of 5 average rating, 104 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 North 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.

Popular amenities for Wellfleet outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

The exterior of a charming cottage is showcased, featuring a picnic table with an umbrella and several adirondack chairs. The dark shingle siding complements the vibrant blue door, while the surrounding lawn is naturally landscaped and leads toward a pathway with kayaks nearby.

4.9 out of 5 average rating, 10 reviews

Sandy beach cottage on Wellfleet Bay

4.95 out of 5 average rating, 37 reviews

The exterior of a charming cottage is presented, featuring a gray wood facade with light blue accents. The front yard is spacious and green, framed by well-maintained bushes and trees. A driveway leads to a detached garage. The inviting entrance is adorned with a small porch.

Home in Eastham

Eastham Cottage Near National Seashore Beaches!

The exterior of the house is framed by vibrant pink flowering shrubs, showcasing a well-maintained yard. Solar panels are positioned on the roof, reflecting a commitment to sustainability. The entrance is marked by a set of steps leading up to a welcoming front door.

4.82 out of 5 average rating, 49 reviews

Beachside National Seashore Home with A/C

Superhost

5 out of 5 average rating, 4 reviews

Charming Garrison Colonial Home in Wellfleet

A serene landscape is displayed with lush green marshlands reflecting the soft colors of the sunset. Gentle waterway patterns create a tranquil ambiance, while trees line the background, enhancing the natural beauty of the scene.

5 out of 5 average rating, 17 reviews

Marsh Side Home with Stunning Sunset View

4.97 out of 5 average rating, 170 reviews

A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

Home in Chatham

The Osprey Nest - Beach house with stunning views

Superhost

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

4.96 out of 5 average rating, 195 reviews

The Sea Captain's Carriage House

4.86 out of 5 average rating, 124 reviews

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.

Home in North Eastham

Walk to Beach, Pet Friendly, New Fenced Backyard!

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 126 reviews

A charming studio cottage with wooden shingles is nestled among trees, featuring a private deck and gas grill. Colorful flowers line the pathway leading to the entrance. A lush green lawn surrounds the building, creating a tranquil outdoor setting.

Apartment in Brewster

Songbird Studio- Secluded but close to everything!

A spacious studio layout is highlighted, featuring a large comfortable sofa and a cozy sleeping area with a patterned blanket atop a queen bed. A kitchenette with modern amenities and wooden accents complements the inviting atmosphere, while natural light brightens the room.

4.91 out of 5 average rating, 148 reviews

Frenchie Studio Apt, Awesome spot!

4.94 out of 5 average rating, 218 reviews

Apartment in Eastham

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

4.83 out of 5 average rating, 121 reviews

Apartment in North Truro

Seasong Cottage

4.9 out of 5 average rating, 122 reviews

An outdoor seating area is presented with a round table and four chairs, shaded by a vibrant red umbrella. A decorative wall hanging and plants add character to the wooden exterior. A surfboard rests against the wall beside the entrance, surrounded by stone and greenery.

Apartment in Eastham

Peaceful retreat in the woods...

The entrance of a two-story condo is framed by lush greenery and neatly trimmed hedges. A stone pathway leads to a welcoming porch, where outdoor seating is arranged among garden beds filled with various plants. The facade features charming gray shingles and a small balcony.

4.93 out of 5 average rating, 107 reviews

Prime Location - Beautiful 2-bd condo, Parking, AC

The quaint cottage features a white exterior with a grey shingled roof, surrounded by lush greenery. A well-maintained front yard adds to the peaceful charm, while a small porch is visible at the entrance, welcoming guests to the serene space.

4.95 out of 5 average rating, 172 reviews

"Sadie by the Bay" cute cottage- short walk to bay

A historic three-story building is showcased, featuring a light yellow exterior complemented by white trim. Large windows allow ample natural light, while a white picket fence surrounds the front yard, providing a welcoming entrance. Mature trees add greenery and shade to the property.

4.98 out of 5 average rating, 180 reviews

Charming 1-Bedroom Condo, Parking, A/C

Condo rentals with outdoor seating

The tranquil waters of the harbor are seen, dotted with various boats gently bobbing on the surface. A barrier of rocks outlines the marina, while the calm blue of the water reflects the soft light of the sky.

4.93 out of 5 average rating, 357 reviews

Beachfront Town Center

A charming exterior view of a two-story Cape Cod building is presented, framed by well-maintained greenery and colorful flowers. A white picket fence borders the entrance, which features stairs leading up to a welcoming porch adorned with umbrellas and seating.

4.8 out of 5 average rating, 371 reviews

Best location in Ptown,1 Bedroom,PARKING/WaterVIEW

A bright living space features large windows providing views of the waterfront. A white sofa and a cozy sitting area surround a circular coffee table. A patterned area rug anchors the space, while light filters in, enhancing the serene atmosphere.

4.99 out of 5 average rating, 110 reviews

Modern Beachfront Condo, Great Views and Location!

A serene bedroom features a spacious bed adorned with a striped blue and white quilt, complemented by an accent pillow with an anchor design. The walls are painted in soft blue and decorated with framed nautical-themed art. Two white doors lead to the closet and bathroom.

5 out of 5 average rating, 108 reviews

Westend one bedroom condo

A front balcony is shown, featuring a comfortable seating area with a woven chair and colorful cushions. Decorative potted flowers, including vibrant red blooms, are positioned along the railing. The wooden flooring and hanging planters contribute to the welcoming outdoor space.

4.98 out of 5 average rating, 268 reviews

Center of Provincetown | The Stay You Deserve

A cozy living area features a dark sofa with patterned cushions and a green accent pillow. A low table holds a remote and a decorative item. A wall-mounted TV displays a program, while framed black-and-white photographs adorn the adjacent wall, complemented by light streaming through partially closed window shutters.

4.95 out of 5 average rating, 137 reviews

ALL ABOUT LOCATION INCLUDING PARKING!

A spacious dining area is presented with a modern table surrounded by six white chairs. Natural light enters through multiple windows, illuminating the comfortable gray sofa and sleek entertainment unit in the background, which features a minimalist fireplace.

5 out of 5 average rating, 161 reviews

Penthouse, waterviews, large deck,steps from beach

A spacious living area features a light grey sectional sofa adorned with blue and white throw pillows. A rustic wooden coffee table is positioned on a woven rug, while an entertainment unit holds a television. Natural light fills the room through two large windows.