
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 G$8,366 GYD 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.

Cozy Lakefront 3 Bedroom 2 bath home on Sand Pond
Imagine waking up to stunning waterfront views of pristine Sand Pond, perfect for boating and fishing. Located just five minutes from a golf club and grocery store. This 3-bedroom, 2-bathroom cottage is ideal for friends and families looking to come together and enjoy the beauty of Maine. When the sun goes down, toast up some marshmallows on the outdoor propane fire pit. If the weather doesn’t want to cooperate then you can enjoy the full kitchen, covered porch, pool table, and stocked bookcase.
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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!
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Beautiful lake house on Tacoma Lakes near Coast
Pets NOT allowed to due host severe allergies. Please find a different home if you have a service animal or be charged separate cleaning fee of $800 Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened-in Porch 3 spring fed lakes Private dock Bring boat or local rental Canoe/Kayaks FirePit,Grille, Lawn chairs Provided: linens/towels/soap/shampoo/detergent Smoke-deck only - NO SHOES inside *Must sign separate water front liability waiver after booking No cameras inside or out
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The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.
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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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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!
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Mirror Pond Cottage
A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.
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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.
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Visit Beautiful Home on Snow Pond
Belgrade Lakes, Maine's premiere lakes region. Beautiful, four season home on 9 mile long, Messalonskee Lake also known as, Snow Pond. Come to experience life the way it should be. Sunrise view, from master bedroom and lakeside deck surrounded by undeveloped wooded shoreline. Swim, canoe and kayak from private dock. Loons, eagles, osprey, and beavers can be your neighbors for a relaxing week at the lake. Open concept kitchen dinning and living room.
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Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)
Enjoy your stay on the banks of Webb Lake in our 2019 hand-crafted log cabin. This cabin is 35 ft from the high water mark and has views of the lake from all three bedrooms. This rental has access to a private beach ( 200 ft) and is in a secluded cove on the lake. For travelers unfamiliar with Weld, Maine, Weld is nested in the heart of the western mountains of Maine. Hiking Tumbledown and Mt Blue are only the beginning of the recreational opportunities.
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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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Private Lake House, Firepit & Amazing Sunset Views
Spring & summer at Lakeshore Point, a private lakefront home on Canton Lake in Maine. Privately set at the end of a quiet lane, this updated modern retreat offers 200’ of pristine waterfront and your own private sandy shoreline. Swim, kayak, and paddleboard by day, then gather around the fire pit at sunset. Thoughtfully designed with a full kitchen, WiFi, and outdoor shower, it’s where family adventure meets relaxed lakeside New England charm.
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Popular amenities for Winthrop waterfront rentals
Waterfront apartment rentals

Stunning Royal Richmond 2 Br Apartment Get Away!
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Welcome to "West Winds at Pemaquid"
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Panoramic Water Views on the Sheepscot
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Two bedroom duplex across st from crystal lake
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Falmouth Waterfront Carriage House Apt
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Deckhouse with Footbridge Views!
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Penthouse Two Master Waterfront Suite with Rooftop
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"Ship Shape": waterfront, cozy studio- downtown
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Waterfront house rentals

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba
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The Loons' Nest: Lakefront oasis w/ hottub
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Farm house, River, Island, animals & private Chef.
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Moss House: A Modern Waterfront Cabin in the Woods
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Maine Waterfront Hideaway
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Lakefront summer getaway for 6
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Quiet Lakefront Home, Fall dates open!
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Sandy Beach on Cobbosseecontee Lake!
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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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Superb Location! Heart of Old Port/Large Apt
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2 Rangeley Lake unit 2 Condo Dock, Kayaks and more
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Coastal Sunrise Condo 2 bd (1 king,1 twin) Balcony
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Town Park Condo A | Downtown Rangeley
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Lovely 2 bedroom updated riverside condo with pool
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When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$57,097 GYD | G$62,535 GYD | G$55,006 GYD | G$59,607 GYD | G$55,215 GYD | G$58,561 GYD | G$62,744 GYD | G$62,744 GYD | G$49,359 GYD | G$50,195 GYD | G$52,078 GYD | G$62,535 GYD |
| 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 |
Destinations to explore
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- Sebago Lake
- Popham Beach, Phippsburg
- Willard Beach
- Pemaquid Beach
- Pemaquid Point Lighthouse
- Coastal Maine Botanical Gardens
- East End Beach
- Sunday River Resort
- Pleasant Mountain Ski Area
- Popham Beach State Park
- Wolfe's Neck Woods State Park
- The Camden Snow Bowl
- Portland Museum of Art
- Maine Maritime Museum
- Rockland Breakwater Light
- Bradbury Mountain State Park
- Reid State Park
- Bug Light Park
- Grafton Notch State Park
- Camden Hills State Park
- Farnsworth Art Museum
- Mt. Abram
- Maine Lighthouse Museum
- Cellardoor Winery





