House vacation rentals in Winter Harbor

4.82 out of 5 average rating, 22 reviews

Historic 1850 Downtown Retreat [Driftwood Cottage]

This Dutch Colonial is THE OLDEST Small Building in Bar Harbor, built in 1850. Originally residing on Cottage Street until it was saved and moved in 2003 when condos were being built on Cottage Street. The entire 2nd Floor is a spacious master bedroom with a large attached bathroom, large walk-in closet, and an indoor and outdoor patio space. The home has 2 living rooms and still boasts many historic aspects to it. The PERFECT Location in the Heart of Downtown, and the ability to walk anywhere!

4.98 out of 5 average rating, 113 reviews

Introducing Beach Point Cottage! Walk Everywhere!

This authentic Bar Harbor Cottage - in the heart of downtown - is completely redone with brand new touches throughout! Be among the first to enjoy "Beach Point Cottage" and its new bathrooms. Restored hardwood floors. New paint. New Appliances! Many listings say "Bar Harbor" but they mean the town. The village is where you want to be - so you can get to everything you want to see and do... by simply walking there! And Beach Point Cottage is located in America's prettiest village: Bar Harbor.

4.97 out of 5 average rating, 129 reviews

Home in Southwest Harbor

CLEAN, spacious, each BR has private full bathroom

This 3 bedroom 3.5 bath home (each bedroom with its own full bathroom) is situated in a private, wooded setting on the edge of Southwest Harbor's bustling village. All on one level, it offers sophisticated yet comfortable furnishings in an open floor plan design. Each bedroom has a full bath. It’s close to several Acadia National Park access points (Long Pond and Echo Lake are both within a 5 minute drive). This home offers extra wide doorways accomodating those with mobility issues.

4.96 out of 5 average rating, 107 reviews

Skipping Stone on Frenchman's Bay Weekly Rental

Our beachfront home is good for families and pets, with open plan, private bedrooms and an enclosed deck. The beach is perfect for cookouts, walking and exploring. We are nestled down a long gravel drive with quiet neighbors. The main floor bedroom (queen bed) accesses a screened sitting area. The downstairs bedroom (walkout basement) has twin beds and futon chair (single). We are 5 miles from the village, 2.5 miles from Acadia Visitor Center, and .5 miles from an Explorer stop.

4.94 out of 5 average rating, 107 reviews

Home in Ellsworth

The Acadia House on Westwood

Relax with the whole family at this tranquil centrally located place to stay. Slowly unwind at this lovingly remodeled entire home. Enjoy a peaceful walk down the quiet family friendly street its nestled on, or quickly arrive at all the areas attractions. The house is located in Ellsworth Maine and although shops, restaurants, local lakes, Acadia National Park and area attractions are only a quick drive away, the home feels soothing, very safe, secluded and welcoming to all.

5 out of 5 average rating, 138 reviews

Renovated Bar Harbor Cottage just blocks from town

Acadia and Bar Harbor await you as does this sparkling clean, renovated cottage on one of Bar Harbor's favorite streets. Your vacation home on Ledgelawn Avenue is just blocks from town. Walk to restaurants, shops, and the ocean. Whether you're here to stroll the island or hike/bike/run, Cedar Cottage has all you need. Relax with your coffee in the sunroom, sitting area, or on the deck; make great meals in the well-stocked kitchen; sleep soundly on Puffy and Casper beds!

Superhost

Home in Southwest Harbor

4.83 out of 5 average rating, 122 reviews

Honeymoon Retreat - Private and Quiet

Surrounded by spectacular scenery, privacy and quiet, the Tree House is the ideal place to start your adventure exploring the riches of MDI and Acadia. The house is perched up high with limited views of Western Way and Cranberry Island from the deck. Relax to the endless chatter of birds and the sounds of boats traveling by. Walk to the oceans edge. Perfect place for two to rekindle and relax. ** The only entrance is via exterior spiral staircase as pictured in photos. **

4.83 out of 5 average rating, 185 reviews

Home in Tremont

Acadia Escape @ Acadia National Park, A/Seafood

This property is perfect for family and abuts Acadia National Park line in Bass Harbor. It is close to all local attraction including Acadia Nat'l Park, Bar Harbor and Trails. Just minutes from the harbor and Acadia Nat'l Park Trail ( Wonderland Trail), This 5BD/3 bath home is located on the quiet side of Mount Desert Island. Property is very private, spacious and a well landscaped both front and back and is at the dead end of the road.

4.95 out of 5 average rating, 122 reviews

The Near EVERYTHING House!

Bar Harbor! Enjoy the benefits of being right in town, walking distance to the best restaurants, bakeries, and spas; but also live where you can access the famous Acadia National Park with ease. The ocean, of course, is also a short walk away should you be desiring a picnic by the sea. (For the High Season (June 21st - September 7th, 2025) stays are by the WEEK ONLY from Saturday - Saturday).

4.79 out of 5 average rating, 110 reviews

Home in Stonington

Island Getaway - 4BR House (Ocean Views)

★ You will be walking distance from downtown Stonington where you can enjoy local shops, artwork and immerse yourself in the island community. A delightful in-town home with views of Stonington Harbor! The property has a large yard with minimal traffic, perfect for families or a friends getaway. ★ Complementary Kayaks Rentals when you stay 3 nights or more!

4.93 out of 5 average rating, 123 reviews

Home in Lamoine

LAMOINE BEACH HOUSE

Stunning ocean front property overlooking Frenchman and Mt Desert island and Cadillac mt. 270 degrees of ocean frontage with sandy beach. Open concept 1st floor with a wall of windows overlooking the ocean. 4 bedrooms, each with expansive water views. Large front deck for relaxing. 20 minute drive to get to acadia national park trails.