House vacation rentals in Winter Harbor

Find and book unique houses on Airbnb

Top-rated house rentals in Winter Harbor

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

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Guest favorite

Home in Jonesboro

4.96 out of 5 average rating, 104 reviews

The Chandler House with private waterfront.

(Long term discounted bookings available, inquire directly.) This newly renovated 3 bedroom/2 bath home is nestled on the tidal waters of Mason's Bay. The Chandler House boasts "all brand-new everything." We took this 1940's Craftsman Style home down to its studs. Brand new kitchen with with granite counters and all new LG appliances. New washer and dryer. High speed wifi with a 55" smart TV. The large rear deck has a hot outdoor shower. Beyond the orchard is the waterfront with a firepit!

Jun 2 – 9

R2,214 ZAR per night

Guest favorite

Home in Mount Desert

4.87 out of 5 average rating, 119 reviews

Thelma's Garden Cottage

***PLEASE NOTE: THELMA’S DOES HAVE AVAILABILITY BY THE WEEK IN JULY & AUGUST! (check in &check out on Sunday), even though Airbnb’s site calendar misleads reader to think otherwise. Please tap on any bold Sunday to continue. Thelma's Garden Cottage, surrounded by the flower and vegetable gardens of the Burning Tree Restaurant, is located in quiet Otter Creek, just 5 miles south of Bar Harbor, and walking distance from the village playground and store, and trailheads in Acadia National Park.

Sep 8 – 15

R4,282 ZAR per night

Guest favorite

Home in Gouldsboro

4.94 out of 5 average rating, 120 reviews

Schoodic Loft Cabin "The Roost" with Kayaks

This playful cabin offers a unique spot to unwind and explore the Schoodic peninsula and Downeast Maine. Kayaks are provided to explore island studded 462 acre Jones pond, a 10 minute walk down a trail. A 10 minute drives brings you to the less visited Schoodic section of Acadia NP, where a network of hiking and biking trails lace the coastal forests and dramatic rocky coast. Nearby Winter Harbor has shops and restaurants and even a ferry across the bay to Bar Harbor and Mount Desert Island.

Oct 27 – Nov 3

R4,236 ZAR per night

Guest favorite

Home in Mount Desert

5.0 out of 5 average rating, 219 reviews

The Arthaus, an eclectic retreat for two

Located on Mount Desert Islands, "Quietside". The cottage features high ceilings and an open floor plan, with a small deck looking into the woods The walls are decorated with original art work by the owner. Our location is central to the island, situated just outside the village of Somesville; 15 minutes to Bar Harbor, 10 minutes to Southwest Harbor by car. Hiking and swimming opportunities are just 5 minutes away by car. The Arthaus is not suitable for pets, despite our love for them.

Oct 30 – Nov 6

R5,406 ZAR per night

Guest favorite

Home in Hancock

4.98 out of 5 average rating, 127 reviews

Water's Edge-Oceanfront with Stellar View

Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

Apr 19 – 26

R6,553 ZAR per night

Guest favorite

Home in Bar Harbor

4.99 out of 5 average rating, 171 reviews

Hulls Cove Cottage

Settled right outside Hulls Cove Village and its entrance to Acadia National Park, this lovely, cozy cottage is minutes from downtown Bar Harbor and its shopping, restaurants, kayaking and other activities. A classic New England shingled cape, you'll feel right at home in the updated living space, with an upstairs queen bedroom, loft with twin beds, and private backyard. Centrally located to take advantage of everything Mt. Desert Island has to offer!

Jan 2 – 9

R5,873 ZAR per night

Guest favorite

Home in Winter Harbor

4.86 out of 5 average rating, 155 reviews

Cozy Waterfront Cottage. Henry Cove, Winter Harbor

Right on the water — so close, it's like being on a boat — with great view of the harbor. Sit at the table, watching seagulls, bald eagles, the tide coming in and out — Downeast Maine at its best. 3 bedrooms, sleeps 5 (one room with a queen bed, one room with a double bed and one room with 2 twin beds), 1.5 baths.. A short walk to town. Guests return. The house is a comfortable family home, neat and clean, but not fancy.

Dec 24 – 31

R6,147 ZAR per night

Superhost

Home in Gouldsboro

4.86 out of 5 average rating, 105 reviews

Home away from Home

Nestled in a quiet location! Screened in balcony to enjoy the view! Cleared path to the oceanfront to enjoy sun bathing or sea glass hunting Not far from Schoodic Acadis National Park which offers some serene hiking and biking paths Two ferries located in Winter Harbor to go exploring in Bar Harbor There are several fantastic Restaurants I have left plenty of local information at the property

Mar 15 – 22

R8,737 ZAR per night

Guest favorite

Home in Bar Harbor

4.93 out of 5 average rating, 215 reviews

Hulls Cove Hideaway.

Located about a 1/4 from groomed X-country ski trails. Thank you for considering the Hideaway for you stay. The house is well equipped for your comfort. Located near the Hulls Cove park entrance and beach. The calendar does reflect availability, please believe the calendar, if it won't let you book the dates you are looking for that does mean it is not available.

Jan 17 – 24

R3,450 ZAR per night

Guest favorite

Home in Brooks

4.9 out of 5 average rating, 201 reviews

Cedar Swamp Farm

A 2 bedroom house with a porch and gazebo in the back yard in a rural setting located on gravel road. Overlooking lovely horse pastures and deer often come to visit. 35 additional wooded acres to explore. There are unorganized trails that abut “Dead Brook“ available to walk. “Majic”, “Wally” and “Boots” are your neighbors and love to say hello and get a pat.

Jan 17 – 24

R2,157 ZAR per night

Guest favorite

Home in Gouldsboro

4.94 out of 5 average rating, 123 reviews

The Adventure House

Our house was named “The Adventure House” by a family of houseguests with 3 fun and lively children. They told us that their time in Maine was filled with fun adventures so the kids started calling the house “The Adventure House” during their stay. We thought that was fitting as we are so close to Acadia National Park and many other pathways to adventures!

Dec 10 – 17

R2,963 ZAR per night

Guest favorite

Home in sullivan

5.0 out of 5 average rating, 139 reviews

Plovers Cottage, Waterfront

Plovers Cottage on Taunton Bay near Bar Harbor and Acadia Ntl Park provides waterfront living to enjoy swimming, kayaking, and nature up close! Shorefront home with fireplace for cool evenings, spectacular sunset views, all 1linens, kitchen, laundry..... type this in to Youtube search box for arial video! -q9pfaODbcY.

Nov 12 – 19

R5,471 ZAR per night