Vacation rentals with outdoor seating in Winthrop

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Top-rated outdoor seating rentals in Winthrop

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
The treehouse structure is illuminated at dusk, highlighting its elevated design among tall trees. Soft lighting from the windows enhances its cozy appearance. A spacious deck can be seen extending from the building, inviting relaxation amidst the surrounding forest.
Treehouse in Appleton
4.97 out of 5 average rating, 402 reviews

BREEZE, in a tree The Appleton Retreat

BREEZE Treehouse, at The Appleton Retreat is located on 120 acres of private land, bordered by 1,300 acres of a protected nature conservancy. To the south is the Pettengill Stream a resource protected area and to the north a large secluded pond. BREEZE guests may reserve the wood fired cedar hot tub and the sauna, which are close by and private, at an additional charge. The Appleton Retreat is less than a 30 minute drive to Belfast, Rockport, Camden and Rockland, charming downeast seaside towns.

Top guest favorite
Cabin in Chesterville
5 out of 5 average rating, 160 reviews

Off-Grid A-Frame - Peaceful w/ Wood Fired Hot Tub

Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- excellent swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)

Top guest favorite
A spacious private room features a large bed adorned with soft bedding, flanked by modern lamps. Natural light streams in through the door, which opens to a serene outdoor view. A decorative pillow with a sunflower adds a touch of color to the space.
Guest suite in Monmouth
4.97 out of 5 average rating, 195 reviews

Welcome to The Nest - 1 bed, deck w/bath & parking

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

Top guest favorite
A bright eat-in kitchen area features a small wooden table with two chairs. Natural light streams through large windows, providing a view of the lush garden. A washer and dryer are positioned nearby, enhancing the functionality of the space.
Apartment in Bath
4.96 out of 5 average rating, 146 reviews

1820s Maine Cottage with Garden

Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Superhost
A modern tiny house is nestled among tall trees, showcasing two large glass walls that allow sunlight to stream inside. The cabin is elevated on stilts, with a snowy landscape surrounding it, creating a serene and private retreat in nature.
Tiny home in Jay
4.94 out of 5 average rating, 253 reviews

Forest Bathing: Off-Grid Tiny Home, Pond w/ Kayak

Immerse yourself in our forest and serene pond. Quiet 40-acre commune consists of two tiny house cabins + barn on private pond. Book one of the simple yet elegant cabins/barn for more guests. Modern, off-grid, solar-powered retreat. Two solid glass walls to bring you closer to nature while staying in our simple yet elegant tiny house with all comforts of home. 5 min walk to shared fire pits, kayaks, pond & seasonal picnic shelter. AWD SUV or truck required. Off-grid, so no A/C. Pet fee $150.

Top guest favorite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 187 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favorite
A private cottage is surrounded by lush greenery, nestled among trees. The entrance features a wooden deck with two chairs and a small table, inviting relaxation. A well-maintained stone path leads to the cottage, enhancing the private and secluded ambiance.
Cottage in Farmington
4.98 out of 5 average rating, 196 reviews

The cottage at Marble Farm.

This beautiful private cottage is the perfect place to unwind after a long day of adventure! New, bright and comfortable, this secluded cottage is conveniently located just 40 minutes from Sugarloaf, 50 minutes from Saddleback and 10 minutes to downtown Farmington. Feel free to walk, fat bike or x-country ski on nearly 4 miles of groomed private trails located just outside your front door! Contains a full kitchen for meal prep, as well as high speed internet, and climate control.

Top guest favorite
A spacious bedroom features a large bed with blue bedding against a dark blue accent wall. Two bedside lamps provide soft lighting. A comfortable leather armchair is positioned next to a small nightstand, which holds a tissue box and a framed print.
Home in Hallowell
4.98 out of 5 average rating, 170 reviews

Hallowell Hilltop Home and Hot Tub

Discover this newly renovated 2-bedroom, 1-bathroom home in a quiet family-friendly neighborhood in Hallowell. This home's rustic-modern design, natural light, and all-new amenities make it a perfect getaway. Relax in the hot tub, grill on the deck, enjoy the backyard or visit downtown Hallowell and explore its restaurants, cafes, live music and antique shops. This home is also minutes away from several hiking and walking trails that can all be found in our guidebook.

Top guest favorite
An aerial view captures a secluded log cabin surrounded by lush greenery on a private island. A wooden dock extends over the tranquil water, providing access to the cabin, which is nestled among trees. Sunlight glistens on the lake's surface.
Island in Monmouth
4.98 out of 5 average rating, 258 reviews

Naughty Dog Private Island Log Cabin

Be alone with your pup enjoying leash freedom on this remote island. Your 1400 acre backyard is Annabessacook Lake. Enjoy pristine surroundings, a rustic, off-the-grid log cabin, with solar lighting and a hot shower. Swimming, boating, fishing, birding, and relaxing by the fire - do it all (or not). Prepare for adventure! Pack light: Bring your vacay clothes, pups, favorite food, & be ready for a blissful, private island get away. It's AWAY away.

Superhost
A comfortable room features a full size bed with a floral quilt. In one corner, a reading chair displays a colorful striped pattern. A desk with a lamp is positioned nearby, alongside a dresser equipped with a coffee maker and other amenities. Natural light filters through a window adorned with curtains.
Guest suite in Hallowell
4.86 out of 5 average rating, 205 reviews

Room B with private entrance, bathroom & hot tub

Room B has a full size bed with luxury mattress and private bathroom with towel warmer & glass shower. The room includes a desk, TV, minifridge, microwave, coffee maker, dresser, reading chair & private entrance. In the summer we have bicycles to use on the rail trail and kayaks for the Kennebec River. Year round hot tub. Downtown is just a block away where there are numerous restaurants and pubs with live music. Hiking trails & waterfalls nearby.

Top guest favorite
The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.
Guest suite in Conway
5 out of 5 average rating, 354 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Top guest favorite
A cozy cabin interior features warm wooden walls and flooring. Twinkling string lights adorn the ceiling, creating a soft glow. A comfortable armchair is positioned beside a small lamp, with a spacious bed visible in the background, framed by large windows allowing natural light.
Cabin in Lovell
4.97 out of 5 average rating, 379 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking.

Popular amenities for Winthrop outdoor seating rentals

Quick stats about vacation rentals with outdoor seating in Winthrop

  • Total vacation rentals

    Explore 40 vacation rentals in Winthrop

  • Nightly prices starting at

    Winthrop vacation rentals start at G$12,544 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,240 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Winthrop vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winthrop rentals

  • 4.9 Average rating

    Winthrop stays are highly rated by guests—averaging 4.9 out of 5!