Holiday rentals with outdoor seating in Wellfleet

4.93 out of 5 average rating, 113 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 North Truro

Unique Waterfront Artist Cottage

Once a horse stable, Lil Rose now sleeps up to five just a short walk from a private beach. PLEASE READ BEFORE BOOKING: Rentals in season (April-October) are only offered by the week (Saturday-Saturday). November rentals are offered with a 4-night minimum. Rentals December-March are offered with a 3-night minimum. Pets are accepted (max 2) but you MUST let us know in your booking request about your pet so that we can prepare the property. There is a PET FEE that must be paid prior to check in.

4.98 out of 5 average rating, 105 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.

4.9 out of 5 average rating, 187 reviews

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.

Home in Wellfleet

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.

Tiny home in South Yarmouth

A charming cottage is surrounded by lush green trees and shrubs, set within a spacious yard. A gravel pathway leads to the entrance, while a wooden fence provides privacy. Flower boxes add a touch of color to the exterior near the windows.

4.89 out of 5 average rating, 635 reviews

Romantic Cottage w/ Bikes, Paddle Boards & Kayaks

This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

4.97 out of 5 average rating, 191 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, 171 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.

4.9 out of 5 average rating, 247 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.

4.87 out of 5 average rating, 120 reviews

A bright living area features a high cathedral ceiling with wooden beams. Two comfortable sofas are arranged around a coffee table, and a wood-burning stove is positioned beside large glass doors that open to the outdoor deck. Natural light streams in from the windows.

Home in Wellfleet

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!

Superhost

The cottage's exterior is framed by lush greenery, featuring a spacious deck with a large blue umbrella and picnic table. Vibrant flower pots add color, while stepping stones lead towards the entrance, inviting guests to enjoy the peaceful surroundings.

Cottage in North Eastham

4.9 out of 5 average rating, 239 reviews

Classic Cape Cod Cottage

No cleaning fee! 15 min walk to the best bayside beach, Thumpertown Beach. The cottage is in a very peaceful wooded setting. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore. Please note, from June 13 to September 6 we have a 7 night minimum from Saturday to Saturday.

4.86 out of 5 average rating, 564 reviews

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

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

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

4.96 out of 5 average rating, 129 reviews

A serene beach scene is captured, featuring calm waters reflecting a clear blue sky. Grass and low vegetation frame the foreground, leading to gently sloping sandy shores. In the distance, the outline of an island is visible against the horizon, contributing to the tranquil atmosphere.

Bungalow in Wellfleet

Beach Bungalow - Cape Cod Classic

Artwork, Antiques, Beach, Backyard, Privacy This cottage has everything you can imagine and more. Well stocked and maintained. Cape Cod charm and modern amenities. Responsive owner and close to everything - town, harbor, restaurants, park, and of course Mayo Beach footsteps away. Next-door is Beach Bungalow #2 - see link below. airbnb.com/h/beachbungalow2 “Copy/paste link above to your browser.”

Popular amenities for Wellfleet outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.95 out of 5 average rating, 298 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

5 out of 5 average rating, 26 reviews

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.

Home in Wellfleet

The Wellfleet Beach House. Sleeps 6

5 out of 5 average rating, 20 reviews

A spacious open-concept kitchen and dining area features light wooden cabinetry and a central island. A dining table with seating for six is highlighted, while a comfortable living area with a gray sofa and decorative cushions is visible in the background. Natural light floods the room, enhancing the warm wood flooring.

Home in Eastham

Lovely House 5 Min to Beach - Deck, Grill, Garage

4.99 out of 5 average rating, 370 reviews

A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.

Home in Yarmouth Port

Fabulous Waterfront with Spectacular Sunset Views!

4.98 out of 5 average rating, 111 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich Port

Spacious Modern Cottage, beach& Wychmere <1.4mile

4.94 out of 5 average rating, 254 reviews

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

Waterfront Spa|Hot Tub+Cold Plunge in Lake|King bd

5 out of 5 average rating, 12 reviews

An outdoor dining area features a large table surrounded by chairs under a shaded umbrella. A grill is visible in the background, while a view of the ocean is framed by greenery. The area is bathed in natural light with a clear blue sky overhead.

Home in North Eastham

Bay Dreams! Panoramic Bay Views!

4.89 out of 5 average rating, 196 reviews

A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.

Home in Hyannis Port

Cottage with private beach in Hyannis Port

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 123 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!

Apartment in Harwich Port

A charming cottage is nestled against sandy dunes, featuring a covered porch with seating. The exterior showcases light grey shingles, and a large circular decorative element is centered on one wall. Beach chairs are positioned near the entrance, inviting relaxation with ocean views.

4.81 out of 5 average rating, 110 reviews

Cape Cod Beachfront 2 bedroom Cottage Harwich

4.93 out of 5 average rating, 210 reviews

Apartment in Eastham

The Lotus-Hot Tub/Kayaks/Ebikes/Waterfront

4.87 out of 5 average rating, 165 reviews

A sandy path leads from the dunes to the clear blue waters of Cape Cod Bay. Green grasses and shrubbery frame the scene, while a small boat is anchored in the calm sea, suggesting a peaceful beach atmosphere.

Apartment in Dennis

Peace By The Bay

Apartment in Provincetown

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, 167 reviews

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

Apartment in Provincetown

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, 179 reviews

Charming 1-Bedroom Condo, Parking, A/C

Apartment in Provincetown

A bright, open living space features large windows that allow natural light to fill the room. A comfortable couch with decorative pillows sits alongside a classic wooden chair. Brick and wood beams contribute to the rustic charm, complemented by original artwork on the walls.

4.98 out of 5 average rating, 100 reviews

Waterfront with Views & Kitchen-Preston Cross Hall

4.97 out of 5 average rating, 123 reviews

An open living area showcases a cozy seating arrangement with a light-colored couch facing a wall-mounted 4k OLED TV. A round wooden coffee table sits in the center, surrounded by a vibrant flower arrangement. Bright natural light filters through, creating a welcoming space.

Apartment in Hyannis

Ensign Suite | Nantucket Boat | Hyannis + Parking

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, 313 reviews

Modern Provincetown Condo.

Superhost

A serene waterfront view displays calm waters under a clear blue sky. A private beach area is visible with deck chairs and umbrellas arranged neatly on a sandy spot. Lush green gardens and a winding stone path add to the natural beauty of the setting.

4.84 out of 5 average rating, 111 reviews

Bayshore11 Waterfront Renovated Condo with parking

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, 107 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, 102 reviews

Westend one bedroom condo

4.87 out of 5 average rating, 118 reviews

An open-concept living area features a spacious blue sectional sofa and a flat-screen TV mounted on the wall. Natural light floods the room through large windows, offering views of the surrounding greenery. A decorative plant and a textured area rug add warmth to the space.

Condo in Chatham

Steps to Private Beach in Chatham

A welcoming living area features a navy blue sofa facing a stylish fireplace. Natural light fills the space through multiple windows, highlighting a patterned area rug. Unique artwork and modern furnishings, such as a side table and armchairs, enhance the room's inviting atmosphere.

4.98 out of 5 average rating, 168 reviews

Recently updated 2BD with 2 Decks and Water Views

4.88 out of 5 average rating, 104 reviews

The kitchen features white cabinetry and stainless steel appliances, with a large granite island equipped with seating. Natural light floods in from the adjoining dining area, enhanced by multiple windows that offer views of the surrounding greenery.

Condo in Chatham

Walk to beach! Chatham Luxury near downtown, CBI!

The living area features a dark sofa and light wood flooring. Large glass doors open onto a private deck with water views. Two outdoor chairs are positioned on the deck. Bright artwork adorns the walls, complemented by natural light from the windows.