
Waterfront vacation rentals in Winthrop
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Winthrop

Total vacation rentals
Explore 50 vacation rentals in Winthrop

Nightly prices starting at
Winthrop vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 1,430 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 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!
Top-rated waterfront rentals in Winthrop
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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.
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Lakefront Home with Dock | Porter Lake | Sugarloaf
Lakefront paradise on Porter Lake with a private dock, swim float, spacious yard, hammock, deck, patio, grill, fast WiFi, smart TVs, and all the comforts of home. Enjoy direct access to Maine’s ATV and snowmobile trail network right from the property, plus excellent fishing, boating, kayaking, swimming, & ice fishing. Just 20 minutes from Farmington and 35 minutes from Sugarloaf Resort and the Bigelow Mountains. Experience Maine lake living at its finest in every season with stunning lake views
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Quiet Lakefront Home, Private Dock!
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!
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Glass Wall Waterfront Hot Tub Fireplace Tiny Home
Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis
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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.
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Forest Bathing Lake Tiny Home: Kayak Fish Fire Pit
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 $89.
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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!
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Spacious Downtown Hallowell River View Apartment
★ Spacious 1,600 Sq Ft ★ Downtown view on one side, River View on the other ★ King Bed, Queen Beds, and two high quality folding beds ★ Washer and Dryer ★ Private entrance on both river side and and downtown side ★ Private parking behind building ★ Wi-Fi High Speed Fiber Optic ★ 65" Roku TV ★ Close to the beautiful Vaughn Woods and Rail Trail ★ 5 minutes to Augusta ★ Centrally located and 1 hour to the coastal towns of Belfast, Camden, Rockland, or Portland Happy humans are welcome!
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Lakeside retreat on quiet cove on Cobbessee Lake!
Nothing beats summer days on the lake in Maine. Not only is this lake home situated on a quiet cove on central Maine's Cobbossee Lake, but it is near amenities in Augusta and close to I-95! Enjoy two large docks, a large lawn and gently sloping swimming area, and a newly renovated five bedroom house with two full bathrooms. This is the Maine vacation home you are looking for! Two of the bedrooms and one bathroom are in the basement, which is still under some small construction.
BeachViewCleanliness

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit
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.
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Wren Cabin + Wood fired Sauna
We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.
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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.
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Popular amenities for Winthrop waterfront rentals
Waterfront apartment rentals

Panoramic Water Views on the Sheepscot
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On The River 2 with Lucy the resident cat
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Welcome to "West Winds at Pemaquid"
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Beekeeper's Cottage- Peaceful,Quiet - Ocean Front
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Stunning Royal Richmond 2 Br Apartment Get Away!
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"Ship Shape": waterfront, cozy studio- downtown
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Two bedroom duplex across st from crystal lake
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Standish Country Setting
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Waterfront house rentals

Veedon Fleece on the Lake
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The Modern Lakehouse
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Lakefront: Private Hot Tub, Sauna & Free Massages!
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Brook Ridge Retreat
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Mirror Pond Cottage
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Beautiful lakehouse 2.5 h Boston, 40 min Portland
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Riverside
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The Loons' Nest: Lakefront oasis w/ hottub
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Waterfront condo rentals

Rustic Willard Beach condo ten mins from Old Port!
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Charming, newly remodeled space atop Munjoy Hill.
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Waterviews|Sunsets|Boothbay Harbor
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4 Rangeley Lake unit 4 w/dock kayak & paddle board
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Superb Location! Heart of Old Port/Large Apt
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Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony
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Saddleback | 15 Clubhouse | Ski in/out, Pet friend

The Bailey Island Condo - The perfect seaside retr
ViewHospitalityIndoor spaces
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,003 | ﺩ.ﺇ 1,098 | ﺩ.ﺇ 966 | ﺩ.ﺇ 1,047 | ﺩ.ﺇ 970 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 1,102 | ﺩ.ﺇ 867 | ﺩ.ﺇ 881 | ﺩ.ﺇ 914 | ﺩ.ﺇ 1,098 |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
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- Sebago Lake
- Popham Beach, Phippsburg
- Willard Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- East End Beach
- Coastal Maine Botanical Gardens
- Sunday River Resort
- Popham Beach State Park
- Pleasant Mountain Ski Area
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Rockland Breakwater Light
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Bug Light Park
- Farnsworth Art Museum
- Grafton Notch State Park
- Reid State Park
- Camden Hills State Park
- Mt. Abram
- Cellardoor Winery
- Maine Lighthouse Museum





