Waterfront vacation rentals in Winthrop

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Winthrop

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Bright open four-season guest house with fantastic view of Jones Cove and the open ocean in beautiful South Bristol, Maine. The guest house offers privacy and independence. The top floor has an open space with kitchen, sleeping area with queen bed, bathroom. The ground floor has a desk, Smart TV, seating area and French doors that open onto a stone patio. Includes Kohler generator, fiber optic wifi, outdoor grill & fire pit. The water is tidal Owner lives on property (150 ft from guest house)

Mar 27 – Apr 3

ﺩ.ﺇ568 per night

Guest favorite

Apartment in Richmond

4.92 out of 5 average rating, 120 reviews

Stunning Royal Richmond 2 Br Apartment Get Away!

Beautifully renovated large 2 bedroom apartment in historic Richmond ME. Pack a picnic and take the ferry over to explore stunning Swan Island located right down the street. Excellent spot to put in for paddle boarders and canoes alike as well. After a day of fun saddle up for a pint at The Old Goat pub downtown. Kimberly's Restaurant and Lounge as well as Annabella's Bakery & Cafe are delicious local spots as well. Located 45 min from Portland and 45 min from Rockland our place is perfect

Feb 12 – 19

ﺩ.ﺇ530 per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 173 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

May 4 – 9

ﺩ.ﺇ421 per night

Guest favorite

Cottage in Sabattus

4.96 out of 5 average rating, 102 reviews

Maine lakehouse- close to Portland, 2.5 hr. Boston

Beautiful lake living: 2.5 hours from Boston, 45 min. from Portland. This cozy 2-bedroom home on Lake Sabattus with 110 feet of private lake frontage, sleeps four. All the amenities of home incl. a SS kitchen with newer appliances, air conditioning. Minutes to Lewiston/Auburn - close to dining and stores. Spend your days swimming, canoeing, kayaking and fishing, use our grills or lobster pot to prepare your dinner and relax by the fire pit, toasting s'mores while watching the gorgeous sunsets.

Dec 15 – 22

ﺩ.ﺇ589 per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

Dec 15 – 22

ﺩ.ﺇ590 per night

Guest favorite

Loft in West Gardiner

4.98 out of 5 average rating, 113 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

Jun 27 – Jul 4

ﺩ.ﺇ461 per night

Guest favorite

Farm stay in Norway

4.96 out of 5 average rating, 152 reviews

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

Nov 13 – 20

ﺩ.ﺇ516 per night

Guest favorite

Home in Belgrade

4.99 out of 5 average rating, 105 reviews

SkyView Treehouse- Luxury Waterfront Retreat

With direct access to Belgrade stream & Messalonskee lake, this treehouse is nestled within the pine trees on the waterfront of Belgrade Stream. Located 20 mins away from Colby College, we welcome families of students to come and stay with us during such a monumental transition. We are 10 mins from the Maine State Capitol, 10 mins from downtown Belgrade Lakes, an hour from Acadia National Park, and one hour, 20 mins from Sugarloaf. Our space is ideal for all vacationers looking for a getaway.

Jan 5 – 12

ﺩ.ﺇ2,052 per night

Guest favorite

Home in Litchfield

4.92 out of 5 average rating, 113 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

Nov 26 – Dec 3

ﺩ.ﺇ849 per night

Guest favorite

Island in Monmouth

4.98 out of 5 average rating, 194 reviews

Island Glamping in a Luxury Tent in Maine

The Hemlock Haven tent overlooks Annabessacook Lake. Sleep comfortably, cook your favorite meals, nap in the hammock, bask in the glow of the fire or woodstove, listen to the calls of the loons, play on the rope swing, canoe or kayak the lake, and walk the trails of this 14 acre wooded island. We greet you at our dock on shore, ferry you and your gear to the island, and ease you into island-life until you are settled. Enjoy super clean, Superhost, Maine Guide hospitality.

Jul 1 – 8

ﺩ.ﺇ545 per night

Guest favorite

Cottage in Sidney

4.91 out of 5 average rating, 101 reviews

Waterfront Cottage

The Waterfront Eagle Pine Cottage sits directly on Snow Pond, just 15 minutes from Colby College and downtown Waterville and 1/2 mile from the New England Music Camp. Enjoy the BEST sunset views from the private dock and listen to the waves and loons at night. The private front deck is the perfect spot for a sunset cocktail after a day of swimming and kayaking from the sandy beach. You also have an outdoor hot soaking tub and access to barrel sauna. Paradise!

Sep 26 – Oct 3

ﺩ.ﺇ1,467 per night

Guest favorite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

Our secluded, very quiet and private two bedroom cabin with loft features a bug-free screened-in porch on its large deck. The cabin overlooks peaceul Sandy Pond, inhabited by bald eagles, loons, and herons. Watch beautiful sunrises and sunsets, and swim, fish and kayak from our dock. We're close to coastal Belfast, Unity, MOFGA (annual Common Ground Fair), Waterville, Acadia and Camden. Eat at The Lost Kitchen, visit the Amish, hike the Hills to Sea Trail.

Dec 10 – 17

ﺩ.ﺇ302 per night