Waterfront holiday rentals in Winthrop

4.96 out of 5 average rating, 214 reviews

A large blue house with multiple sections is pictured beside a clear lake. A private dock extends into the water, and outdoor seating in the form of two chairs is visible on the lawn, surrounded by lush trees.

Home in Augusta

Lakefront: Private Hot Tub, Sauna & Free Massages!

Make memories at our updated, 2500 sq. ft., lakefront home. Use our kayaks, canoes & peddle boats for the family! Great fishing - 648 acre lake. We offer many outside games, range of indoor games & arcade systems. Amazing 4-seasons room with outdoor dining setup viewing the lake. Enjoy our new hot tub, and grilling deck right outside master bedroom. Lavish soaking tub in master bath. Only 4 minutes to golf, 10 minutes to capital city, Augusta, and 45 minutes to skiing as well as Atlantic Ocean!

4.91 out of 5 average rating, 584 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

4.99 out of 5 average rating, 113 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, 518 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, 204 reviews

Cabin in Georgetown

Private Sauna+Near Best Beach+FirePit+Pond+FirePit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin 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 and separated by a privacy screen and natural landscaping.

4.84 out of 5 average rating, 252 reviews

A glamping Geodome stands elevated against a twilight sky, illuminated by warm lights. A small fire burns in a metal pit near a seated figure. Surrounding trees add greenery to the serene outdoor setting, creating a calming atmosphere.

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, 179 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!

4.94 out of 5 average rating, 362 reviews

A treehouse structure is perched on stilts among the trees, surrounded by lush greenery. A cozy screened-in porch with rockers is visible, along with a private wood-fired cedar hot tub on the deck. Steps lead down to the wooded area below.

Treehouse in Georgetown

Modern Treehouse with hottub + Water Views

Experience the airiness of life up among the pines. This unique tree dwelling, with its own private attached wood-fired cedar hot tub, is perched atop a 21-acre wooded hillside sloping to beautiful water views. Enjoy the view from the wood-fired cedar hot-tub or the king size bed--through a wall of windows. This treehouse is cozy all year round, especially in winter. Located in a classic coastal Maine village with Reid State Park's beaches and the famed Five Islands Lobster Co.

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.

5 out of 5 average rating, 107 reviews

The cabin is viewed from the water, framed by lush greenery and tall trees. A spacious porch extends across the front, highlighting the cabin's inviting structure, while the calm water reflects the surrounding nature and the bright exterior of the building.

Cabin in Augusta

Price's Point - Cabin on the water

Brand new Cozy Cabin on a small 181 acre pond. Enjoy the cabin feel of knotty pine and a big country porch overlooking the water. Walk in access to the water or ice in the winter. Kayaking, canoeing, ice fishing, snowmobiling and more depending on the time of year. A peaceful location a mile down a private road but 10 minutes away from a grocery store etc. Eagles, loons and fish will be your neighbors as you are in the moment at Price's Point.

Popular amenities for waterfront rentals in Winthrop

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.94 out of 5 average rating, 107 reviews

The exterior of the multi-unit house is shown, featuring a light gray facade and a red roof. An expansive wooden deck is visible on the second level, overlooking the green lawn. Bright flowers adorn the entrance, adding a touch of color to the outdoor space.

Flat in Orr's Island

Shore House, Leona Unit - Ocean Front Property

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.

Flat in Richmond

Stunning Royal Richmond 2 Br Apartment Get Away!

4.98 out of 5 average rating, 126 reviews

Flat in Cape Elizabeth

Beautiful Kettle Cove Apt Steps to Beaches

5 out of 5 average rating, 133 reviews

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.

Flat in Boothbay Harbor

Sail Loft: Oceanfront Apartment on a Pier.

4.96 out of 5 average rating, 410 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.

Flat in Kingfield

On The River 2 with Lucy the resident cat

Flat in Downtown Portland

A modern kitchen features an island with bar stools and white shaker cabinets. Bright lighting is provided by pendant fixtures above. Large windows showcase waterfront views, while a dining area is visible, with a colorful striped rug under the table.

4.96 out of 5 average rating, 140 reviews

Penthouse Two Master Waterfront Suite with Rooftop

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.

Flat 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.

Flat in Wiscasset

Panoramic Water Views on the Sheepscot

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

4.96 out of 5 average rating, 116 reviews

A wooden dock extends into calm water, reflecting the clear blue sky and surrounding greenery. Trees line the shore, creating a serene backdrop for peaceful moments by the water.

Home in Friendship

Maine Waterfront Hideaway

4.89 out of 5 average rating, 160 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

4.98 out of 5 average rating, 170 reviews

A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.

Home in Bridgton

Wren Cabin + Wood fired Sauna

4.9 out of 5 average rating, 115 reviews

Home in Auburn

The Loons' Nest: Lakefront oasis w/ private dock

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

5 out of 5 average rating, 127 reviews

A waterfront view is captured from a deck, showcasing calm waters surrounded by a lush landscape of colorful trees. The bright blue sky reflects on the surface of the creek, while greenery provides a serene foreground.

Home in Bath

Waterfront Farmhouse with Modern Flair!

4.91 out of 5 average rating, 150 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

Waterfront apartment rentals

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.

Apartment in East End

Charming, newly remodeled space atop Munjoy Hill.

4.91 out of 5 average rating, 492 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.

4.9 out of 5 average rating, 124 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, 112 reviews

The Brunswick

5 out of 5 average rating, 6 reviews

Apartment in Rockland

Rockland Central Over Main, downtown living

4.97 out of 5 average rating, 38 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.

Apartment in Edgecomb

Waterfront|Sunsets|Boothbay Harbor