Holiday rentals with outdoor seating in Wellfleet

4.98 out of 5 average rating, 364 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.

Outdoor spacesValueTV

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.

ValueOutdoor spacesBarbecue

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.

LocationOutdoor spacesCleanliness

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, 197 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.

LocationValueCheckout

4.97 out of 5 average rating, 196 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.

ValueOutdoor spacesWalkability

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.

LocationOutdoor spacesQuiet

4.91 out of 5 average rating, 273 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.

LocationOutdoor spacesGetting around

4.87 out of 5 average rating, 101 reviews

The exterior of a cottage is depicted, featuring a stone pathway leading to the entrance. Lush greenery surrounds the building, complemented by a fenced yard. The cottage showcases a combination of wood and shingle siding, with a large window that allows for natural light.

Guesthouse in Wellfleet

Charming renovated Wellfleet Hideaway

Newly renovated bright cheery cottage in Wellfleet's Historic District, steps from the village center. One large sleeping/sitting room with new king size bed and futon sofa, opening onto roomy glass and screen porch with new dining table for eight. New full separate kitchen. NEW Stove and Refrigerator. NEW Bathroom with shower 2021 + an outdoor shower. Outdoor seating and grill. Linens/towels provided for 2 guests. Ideal for a couple or family w/ up to 2 young children.

LocationOutdoor spacesCleanliness

Superhost

An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.

Cottage in South Dennis

4.86 out of 5 average rating, 587 reviews

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

LocationValueBreakfast

4.99 out of 5 average rating, 182 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

Outdoor spacesValueWi-Fi

4.98 out of 5 average rating, 108 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.

LocationValueCleanliness

4.97 out of 5 average rating, 207 reviews

A welcoming living area features a vaulted ceiling with skylights, allowing natural light to brighten the space. A comfortable sofa is positioned near an inviting brick fireplace, complemented by colorful artwork on the walls. A small table holds decorative items, adding character to the room.

Home in Truro

Escape to N. Truro 3BR Pet Friendly

Don't miss this beautiful, pet-friendly, comfy 3 bedroom home that is totally private, filled with beautiful local artwork, and only minutes from the beach. Outdoor shower, 2 fireplaces, vaulted ceilings with skylights, wifi, cable, ping pong, air hockey, 2 full baths, hammocks, built in Bluetooth speaker system and air conditioning! A true chance to get away and live the Cape life!

ValueOutdoor spacesDecor

Popular amenities for Wellfleet outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 6 reviews

Breathtaking Sunset Views over Marsh!

LocationHospitalityNearby

A charming Cape-style residence is surrounded by a spacious green lawn, framed by trees. The house features a sloping roof and a brick chimney, with large windows allowing plenty of natural light. A gravel driveway provides ample parking space.

5 out of 5 average rating, 27 reviews

The Wellfleet Beach House. Sleeps 6

Outdoor spacesLocationLayout

4.97 out of 5 average rating, 76 reviews

The living area features a high wooden ceiling with exposed beams, a cozy seating arrangement on a patterned rug, and a modern coffee table. A brick fireplace adds warmth, while sliding glass doors provide natural light and views of the surrounding trees.

Home in Truro

The Baumhaus: midcentury home with bay views

LocationOutdoor spacesAir conditioning

5 out of 5 average rating, 6 reviews

Home in Eastham

10 min walk to Beach - Amazing View & Huge Deck

LocationOutdoor spacesIndoor spaces

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

ValueLocationBathroom

The cottage exterior is framed by well-maintained gardens and tall trees. A stone pathway leads to a front door, complemented by a skylight above. Solar panels are visible on the left side, outlining the home’s eco-friendly features.

4.98 out of 5 average rating, 53 reviews

Gardens and yard w/ playset; near paths to ponds!

Outdoor spacesLocationWi-Fi

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, 196 reviews

The Sea Captain's Carriage House

LocationValueLayout

4.86 out of 5 average rating, 127 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!

LocationValueParks

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 127 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!

ValueOutdoor spacesLaundry

Apartment in Provincetown

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, 150 reviews

Frenchie Studio Apt, Awesome spot!

LocationOutdoor spacesAmenities

4.94 out of 5 average rating, 223 reviews

Apartment in Eastham

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Outdoor spacesLocationComfort

4.84 out of 5 average rating, 123 reviews

Apartment in Truro

Seasong Cottage

Outdoor spacesLocationAccuracy

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...

LocationValueFamily

Apartment in Provincetown

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.

4.94 out of 5 average rating, 109 reviews

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

LocationValueAccuracy

Apartment in East Orleans

A sandy path meanders through tall grass, leading toward a tranquil sunset in the background. The sun casts a warm glow over the horizon, suggesting the evening calm of the beach area. Soft greens and earthy tones create a peaceful natural setting.

4.95 out of 5 average rating, 324 reviews

Cozy Waterfront Apartment, Private Beach Access

LocationValueIndoor spaces

4.84 out of 5 average rating, 135 reviews

An open living area features light wood flooring with a large window allowing natural light. A comfortable couch is situated near a wooden coffee table. A dining table with chairs is visible, along with a well-equipped kitchen adorned with modern appliances.

Apartment in Brewster

A quiet, private, unique spot in a great location!

ValueOutdoor spacesComfort

Condo rentals with outdoor seating

A modern kitchen features sleek white cabinetry and a bar area with two high-backed stools. Pendant lights hang above the bar, illuminating a tray with decorative items. The space is arranged for convenience, showcasing well-organized counters and appliances.

4.93 out of 5 average rating, 330 reviews

Modern Provincetown Condo.

LocationOutdoor spacesAmenities

Superhost

A small outdoor deck area features a circular green table surrounded by two matching folding chairs. The wooden flooring is weathered, and the view includes distant structures and the ocean beyond, providing an inviting space for relaxation.

Condo in Truro

4.7 out of 5 average rating, 169 reviews

Escape to the Cape! Open for the 2026 Season!

ValueOutdoor spacesParking

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, 111 reviews

Modern Beachfront Condo, Great Views and Location!

LocationOutdoor spacesQuiet

4.74 out of 5 average rating, 39 reviews

A spacious living area features a neutral-toned sofa paired with a patterned area rug. Sunlight filters through three large windows, illuminating the room. A wooden coffee table sits centrally, complemented by a textured armchair. Glass doors lead to an outdoor deck.

Condo in Wellfleet

Privacy in the Heart of the Harbor

LocationOutdoor spacesSleep quality

A serene view from a private deck is presented, showcasing the expansive bay beyond. Two lounge chairs with blue and white striped cushions are positioned for relaxation, while the manicured lawn and beach area are visible, inviting guests to enjoy the outdoor space.

4.9 out of 5 average rating, 221 reviews

Bayshore 2:Direct waterfront/Parking/Pets welcome

Outdoor spacesValueCheck-in

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, 138 reviews

ALL ABOUT LOCATION INCLUDING PARKING!

LocationOutdoor spacesGetting around

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, 163 reviews

Penthouse, waterviews, large deck,steps from beach

Outdoor spacesLocationKitchen

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.