
Cottage vacation rentals in Winter Harbor
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Quick stats about cottage rentals in Winter Harbor

Total vacation rentals
Explore 10 vacation rentals in Winter Harbor

Nightly prices starting at
Winter Harbor vacation rentals start at ﺩ.ﺇ 588 per night before taxes and fees

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Over 500 verified reviews to help you choose

Wi-Fi availability
10 of Winter Harbor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Winter Harbor rentals

4.9 Average rating
Winter Harbor stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated cottage rentals in Winter Harbor
Guests agree: these cottages are highly rated for location, cleanliness, and more.

The Cottage
A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh water.

Stylish ocean-view home on Acadia's Schoodic Loop
This stylish, former 1940s schoolhouse is one of just a few homes located along Acadia's scenic Schoodic Loop; guests can virtually hike or bike by stepping out the back door. Enjoy our crowd-free corner of Acadia or drive 7 min to the ferry for a charming boat ride to Bar Harbor. Alternatively, head up the coast for more hikes, picturesque fishing villages, quirky shops and quintessential Maine culture. At home, enjoy books, original art, a curated record collection and fresh local lobster.

Southwest Harbor Cottage
Enjoy unparalleled views of bustling Southwest Harbor and the beauty of Acadia National Park from the comfort of Eagle's Nest. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll into the village, where you'll find plenty of local shops and restaurants. You can access the water via a set of stairs leading from the property to the shoreline. End your days on the deck and keep your eyes peeled for seals!

Lamoine Modern Guest House
Relax, recharge, & escape here. A unique & peaceful guest house in the woods of Lamoine, Maine with large windows (without coverings) looking out to the woods. Close enough to Bar Harbor/Acadia National Park (45 min) but removed from the chaos. A 10-minute walk down a gravel road to a beach in Lamoine with distant views of Acadia National Park. Enjoy all weather with our new wood stove fireplace surrounded by large windows. We have a comprehensive guidebook for our guests upon check-in.

Lillebo
Lillebo is set near the end of a dead end road with a five minute walk yielding views over Frenchman's bay with Sorrento in the near view and Winter Harbor and Bar Harbor in the long view. This homey house is set about 200 feet from the road with no neighbors in direct view. There’s a screen porch on one end of the house and a garage on the other. In the garage there is a ping pong table, corn hole, darts and bikes. There are three adult bikes, one youth bike and one kids bike.

Shore Haven - Oceanfront Home in Corea by the Sea
Peak Season (July & August 2027): Weekly rentals only, Sunday arrival/departure. Enjoy this charming cedar-shingled cottage with 1,850 sq. ft. of single-level living. Features include an open-concept kitchen, dining, living, and sunroom area with spectacular ocean views, 3 bedrooms, 2 baths, and a library off the main bedroom with a double bed. Beautifully landscaped grounds slope gently to 240 feet of dramatic oceanfront.

Meadow Point Cottage
Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Quiet lakefront cottage on Graham Lake
Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Cottage by Acadia National Park
Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.

Oceanfront Acadia Cottage With Private Beach
Enjoy this charming oceanfront cottage with its expansive panoramic windows. With 175 feet of private oceanfront beach at your doorstep, you'll enjoy unparalleled views of Bass Harbor. Located on the serene "Quiet Side" of Mount Desert Island, this cottage serves as an ideal home base for your exploration of Acadia National Park.

320 Ft Of Private Beachfront w/ Stargaze Platform!
🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance!

The Cadillac at Bay Meadow Cottages
At the foothills of Acadia National Park and in the seaside village of Salisbury Cove, Bay Meadow Cottages offers comfort and convenience. Stay with us and be amongst the adventurous and the young at heart. 5 min to Acadia National Park, 10 min to Bar Harbor.
Popular amenities for Winter Harbor cottage rentals
Cottage rentals with a hot tub

Lakeview Cottage

Waterfront Great Pond Cottage w/ Hot Tub & Deck!

Canoe House Bungalow and Spa Retreat ,Searsport

Beach cottage on Penobscot Bay

Ocean View Lawn Cottage - Newly Renovated 2024

Nashport on the Penobscot

Lakefront Couples Boathouse Retreat

At the edge of the woods near the sea
Pet-friendly cottage rentals

Lake Front-Spa Tub-Fire Pit-Full Kitchen-Canoe

Bayview Cottage on the Atlantic

Stonington Harbor Cottage

Ferry Keeper’s Cottage: Deer Isle (Waterviews)

Harborside~Seaglass Beach~Dock~5 min to Acadia

Peaceful Branch Lake Cabin minutes to Acadia

Cozy Cottage on Frenchman Bay

11 Cute 1Br Acadia Cottage Open Hearth Inn
Private cottage rentals

Sleep next to the ocean in Gouldsboro!

Gordon Cottage on Flanders Bay

Edgewater Cabins #2

Spruce cottage, minutes to Acadia, cozy cabin

Fern Hollow Tiny House

Historic School House now with High Speed Internet

Luxurious Newly Renovated Ocean Front Cottage

Whitetail by the River, Acadia National Park 10m
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