
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.

The Nest at Camp Skoglund
Sitting 125 feet from the east shore of Echo Lake is the Nest at Camp Skoglund. A cozy cottage for two with all of the amenities you will need. Your deck provides a wooded view of the lake and we offer a fully equipped waterfront for your relaxation and fun on the water. A fire pit is also available. If you need lodging for more than 2, please inquire about our other cabin, Pop's (also on AirBnb). We are open seasonally starting in early June until Columbus Day or later depending on the weather.

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!

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.

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

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.

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!

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!

Roxie the Tiny Cabin on 100 acres
If all you need is a bed and a bathroom & hot tub, Roxie is the cabin for you! A comfortable full-size bed, composting toilet, a mini fridge & woodstove and electric heater are here for you in this cozy 8x12 cabin in the woods. 2wd access & a parking spot near your door. Hike trails, kayak, fishing, cross-country skiing, or snowshoeing then return to your little space to relax & enjoy! A firepit with wood, an outside table and hammock chairs. 24/7 Guest restroom with shower

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.

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.

Large Private Waterfront Lakehouse in Maine
NEWLY RENOVATED! Direct waterfront on Lower Narrows Pond. Only 2.5 hours from Boston. Unwind on a pristine lake in Maine at this welcoming, completely private SPACIOUS lake house with over 2000 square feet of living space. Private dock, new winding staircase through the woods down to the dock, paddleboard, water trampoline, gas grill, and firepit. With 4 luxurious bedrooms including 2 king suites, this gorgeous property offers a retreat for the whole family.

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.
Popular amenities for Winthrop waterfront rentals
Waterfront apartment rentals

Stunning Royal Richmond 2 Br Apartment Get Away!

Sail Loft: Oceanfront Apartment on a Pier.

Cottrill House on Damariscotta River #2

Standish Country Setting

On The River 2 with Lucy the resident cat

Stone Mountain Guest House 2nd Floor Apt.

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Panoramic Water Views on the Sheepscot
Waterfront house rentals

Mirror Pond Cottage

Riverside

Beautiful Designer's Hideaway on the Maine coast!

Lakefront: Private Hot Tub, Sauna & Free Massages!

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

Beautiful lake house on Tacoma Lakes near Coast

Private Lake House, Firepit & Amazing Sunset Views

Brook Ridge Retreat
Waterfront condo rentals

Charming, newly remodeled space atop Munjoy Hill.

Saddleback | 15 Clubhouse | Ski in/out, Pet friend

Mabel's Maine Studio on the River

Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony

Waterviews|Sunsets|Boothbay Harbor

Rustic Willard Beach condo ten mins from Old Port!

Superb Location! Heart of Old Port/Large Apt

Full condo 2 bedrooms 2 bathrooms kitchen 3 beds
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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