Vacation rentals in Winthrop

4.97 out of 5 average rating, 393 reviews

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

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.

5 out of 5 average rating, 148 reviews

Cabin in Chesterville

Off-Grid w/ Wood Fired Hot Tub - 4 Kayaks Included

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)

The camp is illuminated at night, showcasing its inviting exterior. A large porch wraps around the structure, surrounded by trees, while a fire pit is visible in the foreground, where guests can be seen enjoying the warmth of the fire.

5 out of 5 average rating, 21 reviews

Perfect Fall Getaway! Lakefront, Firepit, Laundry!

Spacious four-season lakefront camp on peaceful Dexter Pond in central ME. Enjoy great fishing, canoeing, stand-up paddle boarding, kayaking, or relax and watch the sunsets and loons from the large porch overlooking the pond. The home is in a great location close to Winthrop Center and Wayne (10 mins to local grocery store/ farmers market) 30 mins to Augusta/airport. Many hiking trails nearby and lots of other areas to explore. It's beautiful in all seasons. Private dock, firepit, and laundry!

4.98 out of 5 average rating, 183 reviews

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

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.

4.9 out of 5 average rating, 73 reviews

A large, rugged stone fireplace serves as a focal point in the living area, featuring a sturdy mantel decorated with candles and greenery. A wooden staircase curves next to the fireplace, leading to the upper level. A decorative plant is placed in front of the fireplace.

Home in Monmouth

Spacious Lakeside Comfort - Fall/Winter Wonderland

This spacious home is just steps from the shore of Anabessacook Lake. Here you will enjoy the comfort and luxury of a well-equipped house, surrounded by the best of what Maine has to offer. The Red Top House features an incredible stone fireplace, large screened porch, and stone patio with outdoor fire pit. Bedrooms are comfortable with water views. The kitchen is very well equipped for the whole family. Rental includes use of non-motorized boats and firewood. Ice fishing is steps away!

4.95 out of 5 average rating, 63 reviews

A cozy seating area features a soft green couch with tufted detailing, complemented by a striped area rug. A vintage green chest serves as a coffee table, and a floral artwork adorns the wall, adding a touch of color to the inviting space.

Apartment in Winthrop

Jill's Place!

This is a brand new daylight basement airbnb with access to Cobeeseecontee Lake in Winthrop Me. 2 bdrm. 1 with a queen and 2nd with 2 twins. It is decorated with with white shiplap, beautiful hardwood floors and very light and bright. It is 160 ft from the lakeside where there is a very nice grassy area with lounge chairs, a dock, and a swimming area. 1 kayak and a peddle lboat included. 500 ft away from the Travis Mills restaurant "The White duck" 2 miles from the famous Cabin Masters!

4.98 out of 5 average rating, 245 reviews

A spacious dome tent is nestled among tall trees, with sunlight filtering through the leaves, creating a warm glow. The forest floor is covered with soft earth and scattered leaves, enhancing the natural surroundings, while the calm ambiance invites visitors to relax and enjoy the scenery.

Island in Monmouth

Hammock Haven Island Dome

The Hammock Haven Island Dome looks at sunsets on Annabessacook Lake. Sleep comfortably, cook your favorite meals, hammock nap on a dock in the water, bask in the glow of the fire or wood stove, hear the calls of the loons, play on the rope swing, canoe, kayak, or paddle board the lake, explore the trails of this 14 acre wooded island, and then repeat as needed. We greet you at our shoreside dock and help you settle into island-life. Enjoy super clean, Superhost, Maine Guide hospitality.

4.97 out of 5 average rating, 151 reviews

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

Hilltop Retreat with A/C, Hot Tub & Sauna

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 or infrared sauna, 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.

5 out of 5 average rating, 5 reviews

An aerial view showcases the lakefront cottage nestled among trees and a manicured lawn. A wooden dock extends into the calm water, providing access for activities. The spacious deck of the cottage is visible, offering a welcoming outdoor area for relaxation.

Cottage in Manchester

Cobbossee Lake Cottage – 3 Bedroom, 2 Bath

Welcome to your perfect Maine getaway! This charming lakefront cottage on beautiful Cobbosseecontee Lake offers the peace and relaxation you’re looking for, with all the comforts of home. Nestled among tall trees and lush green lawn, this three-bedroom, two-bath retreat is ideal for families, couples, or friends looking to unwind in nature. Whether you’re fishing, kayaking, swimming, or just taking in the tranquil surroundings, this is the lakeside vacation you’ve been dreaming of.

4.97 out of 5 average rating, 199 reviews

A serene landscape captures a vibrant sunset reflected on calm water. The sky displays shades of orange and pink, blending into deep purple hues, while the silhouette of trees lines the horizon. The tranquil scene conveys a peaceful natural setting.

Loft in West Gardiner

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment above our garage. 15 minutes to Gardiner/Augusta, 15 minutes to I95/295. Less than one hour from Portland. Sit by the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and play. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Superhost

A charming cottage is nestled among trees along the lakefront, featuring a sloped roof and large windows. A wooden dock extends into the water, with steps leading up to the home, providing easy access to the serene surroundings.

5 out of 5 average rating, 6 reviews

Serene Lakeside Retreat

Relax with the family at this peaceful lakefront retreat on Cobbosseecontee Lake. Lovingly remodeled with care, this cozy 2-bedroom cottage blends Maine cabin charm with modern updates. Enjoy a full kitchen, spacious living area, two baths, a screened porch, and a deck with stunning lake views. Kayaks included! Unwind, explore, and make lifelong memories at this beautiful waterfront escape.

5 out of 5 average rating, 16 reviews

A serene lakeside view showcases a grassy area with turquoise Adirondack chairs arranged around a stone fire pit. Two kayaks and a paddleboard rest nearby, while a dock extends into the water where a boat is anchored. Tall trees frame the scene, enhancing the natural beauty.

Cottage in Winthrop

Little Landing Cottage Lakefront Dock Kayaks

Cozy lakefront retreat with dock, kayaks, and sunsets. Walk to marina & restaurant. Pet-friendly and peaceful year-round. Slow down, breathe deep, and let the lake carry your worries away. This charming cottage invites you to reconnect—with nature, loved ones, and yourself. Perfect for couples, small families, or close friends seeking a cozy and quiet escape just steps from the water.

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Popular amenities for Winthrop vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Winthrop

5 out of 5 average rating, 9 reviews

Home in Gardiner

The Little Castle

Two individuals sit on a wooden dock, facing a calm lake reflecting a vibrant sunset. The scenery features lush trees lining the shore, while soft clouds scatter across the sky, creating a peaceful and serene atmosphere.

5 out of 5 average rating, 10 reviews

Waterfront Lakehouse in Maine

5 out of 5 average rating, 8 reviews

A cabin with a welcoming yellow exterior is situated on a lakeside, surrounded by greenery. A spacious deck extends from the house, offering seating for relaxation. A private dock leads to the water, and a small bunkhouse is visible in the backdrop.

Cottage in Readfield

Uncle Harold's House

A spacious house is set amidst lush greenery, surrounded by tall trees. A large deck extends from the property, featuring outdoor seating. A picnic table sits on the lawn, providing ample space for relaxation. The clear sky enhances the home's inviting exterior.

4.88 out of 5 average rating, 8 reviews

Dock + Kayaks: Annabessacook Lake Retreat!

Camper/RV in Livermore Falls

A compact camper adorned with a distinctive black and silver exterior is positioned on a paved area surrounded by trees. Two folding chairs are arranged outside, inviting relaxation. An awning extends from the side, providing shade for outdoor enjoyment.

5 out of 5 average rating, 8 reviews

The Moon Root - Kut Away

5 out of 5 average rating, 33 reviews

The cabin's exterior features a welcoming entrance with a sign above the door. Large windows allow natural light, and a small flower pot adds a touch of color beside the entrance. A wooden deck, equipped with two chairs, is surrounded by lush grass and trees.

Tiny home in Winthrop

Lakefront guest cottage,

A view of a serene waterfront area features several boats docked along a calm waterway. Lush green lawns surround quaint cabins nestled among trees, contributing to a tranquil atmosphere. A few lounge chairs are positioned on the grass, offering relaxation by the water.

Cabin in Winthrop

5 out of 5 average rating, 4 reviews

Cozy cabin in a very fun and convenient location.

A wooden dock leads to a waterfront home surrounded by greenery, featuring multiple windows that offer views of the nearby pond. A small boat rests on the shore, with a flag flying near the house. The peaceful setting is enhanced by smooth stones along the water's edge.