Waterfront holiday rentals in Winthrop

4.95 out of 5 average rating, 238 reviews

A beautifully crafted treehouse is illuminated at night, highlighting its wooden exterior and spiral staircase. Soft lights strung in the surrounding trees create a warm ambiance, inviting serenity and connection with nature.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

Cliff House is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

5 out of 5 average rating, 191 reviews

The log cabin, set against a clear blue sky, features a peaked roof and large windows that reflect the natural surroundings. A front porch with a railing extends from the cabin, surrounded by patches of snow and green trees, enhancing its secluded ambiance.

Cabin in Andover

Mountain Time Cabin,Spectacular Views! Secluded!

Looking for a mountain cabin getaway? You have found it here at Mountain Time Cabin! This cabin is new and absolutely beautiful! Located in the Western Mountains of Maine - a true paradise for the outdoor enthusiast. Bring your Snowshoes,Skies,Snowmobiles, or hike right from the front door with a 130 acres of trails to explore. Enjoy the spectacular views of the mountains and the cascading brook all from sitting in the recliners with the warmth of the pellet stove Has AC and pool table.SECLUDED!

4.99 out of 5 average rating, 111 reviews

A bright dining area is illuminated by natural light streaming through a skylight. A wooden table is surrounded by dark chairs, while details such as a hat and a garment hang on the wall. A door leads to the serene outdoor view.

Home in Georgetown

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

4.99 out of 5 average rating, 517 reviews

A cozy cabin is nestled among snow-covered trees, showcasing a wooden exterior in warm tones. The entrance features a welcoming pathway lined with snow, while the nearby deck offers a glimpse into the winter landscape, creating a serene atmosphere in the snowy environment.

Cabin in Hanover

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

4.99 out of 5 average rating, 161 reviews

The exterior of the house features a brown wood facade with large triangular windows enhancing natural light. A wide deck is adorned with flower pots, surrounded by well-maintained greenery and a grassy lawn, creating a welcoming entrance.

Home in Pittston

Riverside

Overlooking Kennebec River, Riverside is a perfect setting. Open 365 days per year; 2BR, 1 BA, kitchen, DR/common area. Situates 4 comfortably, 6 with the use of couches, 8 with added use of floor mattresses. Renovated, open concept, our home is wheelchair accessible. We accept Service dogs and will consider family dogs and other pets on a case-by-case; please ask. Owners reside on property in separate building. Outdoor trail cameras and AOSU cams in use to monitor exterior of residence only.

5 out of 5 average rating, 204 reviews

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

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.

4.99 out of 5 average rating, 190 reviews

A serene waterfront view captures calm waters reflecting the sky and surrounding landscape. Lush greenery is visible along the shore, while scattered clouds drift across the blue sky. The tranquil scene invites relaxation and appreciation of nature.

Home in Newcastle

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

Waterfront Retreat with Gorgeous Views Stunning 3-bedroom, 2-bath home perfect for multi-generational gatherings. Features an open-concept layout, chef’s kitchen, 1st-floor bedroom and bath, 2nd floor with 2 bedrooms and 1 bath. Kayak from your backyard, hike nearby trails, or swim in Damariscotta Lake just a 5-minute walk away. Stay connected with high-speed fiber optic WiFi. Close to charming Newcastle and Damariscotta shops and restaurants. A true oasis for nature and relaxation lovers!

4.84 out of 5 average rating, 249 reviews

A person is seen kayaking in a vibrant green kayak on a calm stream, surrounded by lush greenery and trees. In the background, the Geodome and deck are visible, creating a serene atmosphere for outdoor activities.

Dome in Buckfield

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

4.98 out of 5 average rating, 176 reviews

The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.

Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

4.95 out of 5 average rating, 177 reviews

A cozy interior features natural wood paneling and beams. Two upholstered chairs are positioned near a large window, allowing light to fill the space. A small bookshelf holds several books, while kitchenware is organized on a nearby shelf. A white stove complements the rustic setting.

Cabin in Bridgton

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

5 out of 5 average rating, 183 reviews

Cabin in Georgetown

Near Beach+Cedar Sauna+Outdoor Shower+FirePit+Pond

Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

Cottage in South Thomaston

An open-concept great room features high wooden ceilings with exposed beams. Large windows provide ample natural light and views of the surroundings. A comfortable seating area includes a sofa and coffee table, while a dining space with chairs is positioned near the kitchen.

4.96 out of 5 average rating, 202 reviews

Timeless Tides Cottage

This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

Popular amenities for Winthrop waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.92 out of 5 average rating, 171 reviews

A welcoming living area is showcased with soft furnishings in varied colors, including a green sofa and light blue armchair. A patterned area rug is placed under a coffee table. Natural light streams through a window adorned with sheer curtains, while a floor lamp and table lamp provide additional illumination.

Apartment in Richmond

Stunning Royal Richmond 2 Br Apartment Get Away!

Apartment in Boothbay Harbor

A welcoming living space features two comfortable armchairs and a soft couch, with a wooden coffee table at the center. Large windows provide abundant natural light and views of the water. A well-equipped kitchen is visible in the background, along with light-colored cabinetry.

5 out of 5 average rating, 133 reviews

Sail Loft: Oceanfront Apartment on a Pier.

Apartment in Damariscotta

4.87 out of 5 average rating, 113 reviews

Cottrill House on Damariscotta River #2

4.96 out of 5 average rating, 409 reviews

A cozy living area is highlighted by an electric fireplace set against a stone wall, providing a warm focal point. Two glasses of red wine sit on a rustic glass table, accompanied by decorative wood coasters and a small plant nearby.

Apartment in Kingfield

On The River 2 with Lucy the resident cat

4.98 out of 5 average rating, 276 reviews

A serene view of Maquoit Bay is displayed, featuring calm, reflective waters under a clear blue sky. Seaweed lines the shore, complementing the natural landscape of distant tree-covered shorelines, creating a peaceful coastal scene.

Apartment in Freeport

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

4.94 out of 5 average rating, 109 reviews

A wooden dining table is set by large windows, offering views of the water and surrounding trees. A blue bowl sits at the center, complemented by placemats in soft blue tones. Natural light fills the space, highlighting the warm wooden floor.

Apartment in Wiscasset

Panoramic Water Views on the Sheepscot

5 out of 5 average rating, 163 reviews

A dark blue oval sign displaying the name 'West Winds at Pemaquid' features an anchor design, indicating a nautical theme. The sign is framed in silver and includes the establishment year '2016,' suspended by a chain against a backdrop of green trees.

Apartment in Bristol

Welcome to "West Winds at Pemaquid"

Apartment in Damariscotta

4.85 out of 5 average rating, 577 reviews

"Ship Shape": waterfront, cozy studio- downtown

Waterfront house rentals

4.92 out of 5 average rating, 129 reviews

Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.

Home in Oxford

Mirror Pond Cottage

4.95 out of 5 average rating, 182 reviews

A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.

Home in Windham

Waterfront Gem walkable to Restaurants!

4.89 out of 5 average rating, 158 reviews

A fire pit is positioned near the water's edge, surrounded by two adirondack chairs. The setting sun reflects off the river, casting warm hues across the sky and water. Green trees frame the tranquil scene, creating a peaceful atmosphere.

Home in West Bath

Oak Leaf

4.92 out of 5 average rating, 151 reviews

The front entrance showcases a vibrant red door framed by two sconces, inviting guests inside. Steps lead up to a spacious deck, which is flanked by decorative flower pots. The house features a classic shingle exterior, accented by charming dormer windows.

Home in Boothbay Harbor

Renovated home with amazing waterfront views

4.92 out of 5 average rating, 140 reviews

A serene view of the Kennebec River is framed by lush green trees. The landscape features a wooden bench in the foreground, overlooking the water, while distant homes and docks are visible across the river. The sky displays a mix of soft colors as clouds gather.

Home in Bath

Spectacular River Retreat with Hiking Trails

4.91 out of 5 average rating, 149 reviews

An aerial view captures a scenic lakeside property surrounded by dense greenery. Two houses sit amid a well-kept lawn, with a dock extending into calm waters. A small boat is moored nearby, emphasizing the lakeside location.

Home in Litchfield

Beautiful lake house on Tacoma Lakes near Coast

4.94 out of 5 average rating, 158 reviews

A spacious farmhouse stands amidst a grassy area, illuminated by warm light from numerous windows. A covered porch extends along the front, featuring wooden chairs. The surrounding landscape includes mature trees providing a natural backdrop.

Home in Starks

Farm house, River, Island, animals & private Chef.

4.94 out of 5 average rating, 230 reviews

A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.

Home in Stetson

Lakefront Log Cabin on Pleasant Lake

Waterfront condo accommodation

4.99 out of 5 average rating, 115 reviews

A bright living area is revealed, featuring large windows that allow natural light to fill the space. A cozy gray sofa and matching armchair are complemented by colorful pillows. A small side table holds a plant, and a soft area rug adds warmth to the hardwood floor.

Condo in East End

Charming, newly remodeled space atop Munjoy Hill.

4.91 out of 5 average rating, 488 reviews

Luxury Beach Front Condo! Prime Location!

A wide sandy beach stretches along the coastline, with gentle waves breaking at the shore. Two figures walk along the water's edge, while a clear blue sky enhances the tranquil atmosphere of the scene.

4.89 out of 5 average rating, 123 reviews

Oceanfront Condo with Awesome Views

A modern living area features a spacious gray sofa and a flat-screen television mounted on the wall. A dining table with four chairs is positioned nearby, while a pattern rug adds texture to the floor. The open layout provides a flow towards the kitchen.

4.93 out of 5 average rating, 14 reviews

Brand new unit 45 Steps to the beach! Sleeps 4

A four-story oceanfront condo building features multiple balconies that overlook a sandy beach. Sunbathers and beach chairs are spread across the shoreline, with a vibrant atmosphere enhanced by people enjoying the coastal setting under a partly cloudy sky.

4.84 out of 5 average rating, 110 reviews

The Brunswick

5 out of 5 average rating, 6 reviews

Condo in Rockland

Rockland Central Over Main, downtown living

4.97 out of 5 average rating, 36 reviews

A serene waterfront scene captures a dock curving toward a hazy sunrise over the water. Soft clouds scatter in the sky, reflecting gentle hues of orange and yellow, while a bridge is visible in the distance. Green grass and reeds frame the tranquil setting.

Condo in Edgecomb

Waterfront|Sunsets|Boothbay Harbor