Cottage vacation rentals in Winter Harbor

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Top-rated cottage rentals in Winter Harbor

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Guest favorite

Cottage in Trenton

4.97 out of 5 average rating, 331 reviews

NEW Whitetail Cottage, Acadia National Park 7m

NEW Whitetail Cottage East only 6.9 mi to Acadia National Park Maine - a hikers paradise! Centrally located for a perfect Acadia Adventure! Book for the convenient location - stay for the style. Tiny home has WIFI & SMART TV. Off the main(e) drag but nestled in a wooded property 1/2 mile from Bar Harbor Rd/Route 3 down the road from Mount Desert Island and a stones throw from multiple authentic Maine lobster pounds. Perfect for 2 . A short drive to MDI, Acadia, Bar Harbor,Southwest Harbor

Guest favorite

Cottage in Southwest Harbor

4.98 out of 5 average rating, 140 reviews

Southwest Harbor Cottage

Enjoy unparalleled views of bustling SW Harbor and the beauty of Acadia National Park from the comfort of a newly renovated cottage. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll to the village where you'll find plenty of shops and restaurants. Access to the water is easy for those who don't mind a little clamoring down the bluff. End your days on the deck and keep your eyes peeled for seals!

Guest favorite

Cottage in Bucksport

4.91 out of 5 average rating, 182 reviews

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

Need to escape the hustle and bustle or a cramped work from home life? The year-round lakehouse is perfect for the outdoor recreational enthusiast, the work-from-home adventurist, a family trip to Acadia, or a cold-weather spa escape. Enjoy this spacious waterfront home in Bucksport, Maine. Relax in the spa tub, fish from the included canoe and kayak, or work remotely with a view. When you want to explore, the home's location is convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Guest favorite

Cottage in Bar Harbor

4.96 out of 5 average rating, 301 reviews

Ledgewood Grove Cottage in Bar Harbor

Year-round! This tidy cottage comes fully equipped for a pleasant stay in Bar Harbor. The perfect location, tucked off the main road with easy access, puts guests a 10 min. drive from downtown Bar Harbor, and a 6 min. drive from the Acadia National Park entrance and visitor center. This property is located just a few minutes walk from the Free Acadia Shuttle bus route(seasonal). Ledgewood Grove includes a full-size washer/dryer, WIFI, satellite TV, outdoor gas grill, & much more!

Guest favorite

Cottage in Deer Isle

4.93 out of 5 average rating, 336 reviews

Beachfront Guest Cottage - Year-round Hot Tub!

Our cozy guest cottage has easy beachfront/kayak/canoe access, and is located very close (within walking distance at low tide) to the public boat launch for larger boats. Great location to explore Deer Isle, Acadia (approx 1hr), Castine (45m), and the Bangor (1hr) area. Brave children and adults even swim from the beach but comfortable swimming ponds/lakes are 10m in several directions. The hot-tub is open year-round! Additional guests can be considered prior to booking.

Guest favorite

Cottage in Mount Desert

4.99 out of 5 average rating, 144 reviews

Cozy Seal Harbor Cottage

We request anyone who stays on our property be fully vaccinated. Thank you for helping to keep our community healthy! This stand along cottage is on the same property as owner's home and includes 1 parking space. 2 bedrooms with full bath, laundry, and a fully stocked kitchen. House abuts Acadia National Park; Seal Harbor Beach and carriage roads are easy walking or biking distance! Only 12 minutes to Bar Harbor and 5 to Northeast Harbor.

Guest favorite

Cottage in Gouldsboro

4.9 out of 5 average rating, 142 reviews

Shore Haven - Oceanfront Home in Corea by the Sea

*** Peak season- Jun 15 to Sep 14 2025- weekly bookings only with arrival/departure on Sunday***. This cedar shingled cottage home boasts 1850 sq ft of living space on one level. It has open concept Kitchen/Dining/Living/Sun room with spectacular ocean views; 3 bedrooms; 2 baths; and a library/reading room with a double bed. The property is nicely landscaped with a gently sloping lawn to 240 ft. of bold oceanfront.

Guest favorite

Cottage in Lamoine

4.96 out of 5 average rating, 109 reviews

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.

Guest favorite

Cottage in Waltham

4.95 out of 5 average rating, 745 reviews

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

Guest favorite

Cottage in Mount Desert

4.97 out of 5 average rating, 437 reviews

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.

Guest favorite

Cottage in Machiasport

5 out of 5 average rating, 110 reviews

Cliff-perched cottage w private hiking trails

Designed to evoke a ship, this stylish 2BD home overlooks the ocean and is surrounded by 30+ acres of woods, wildlife, and area beaches. 12 of these acres include private hiking tails that wend along the water. Hike, kayak, BBQ, explore Downeast working harbors, or just relax on the deck. Enjoy complete privacy just 17 min from town.

Guest favorite

Cottage in Gouldsboro

5 out of 5 average rating, 145 reviews

Salt Air & Beachfront Breeze Cottage w/ Firepit

Perched On Coastal Waters and Surrounded By Wildlife, Our Cottage Sits On 120 Feet Of Private Shoreline. A True Maine Beachfront Cottage- Only 20 Minutes Drive to the Quiet Side of Acadia National Park at Schoodic Peninsula! Tis The Season! Rocky Beach Cottage Will Be Decorated For The Holiday From December Through January!