House vacation rentals in Winter Harbor

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Top-rated house rentals in Winter Harbor

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Guest favorite

A cozy living room features two light green armchairs positioned across from a decorative wood stove. A mirror hangs above a wooden console, and natural light floods the space through large windows with sheer curtains. A soft area rug anchors the seating area.

Home in Bar 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!

Superhost

The living room features a light-colored sofa paired with two patterned armchairs, complemented by natural light from large windows. A plant sits in the corner, and a textured area rug covers the hardwood floor, creating a welcoming space. Ceiling fans enhance airflow.

Home in Owls Head

4.79 out of 5 average rating, 124 reviews

Bayview- Lobster Dinner included!

Come enjoy this newly updated house! This rental includes a lobster dinner for all guests, caught by a local fisherman and delivered to your door in the same day! Seasonal water views of Rockland Lighthouse. With expansive backyard and deck, great for grilling, lounging and visiting. Local artwork decorate the walls and wood floors run throughout. The kitchen is well stocked for your needs. The rooms are equipped with flatscreen smart TVs with Roku and Amazon Prime. Come experience real Maine!

Guest favorite

The charming exterior of a two-story home is showcased, featuring a yellow facade and a red metal roof. A front porch with steps leads to the entrance, surrounded by greenery and well-kept landscaping. Power lines and trees are visible in the background.

Home in Bar Harbor

5 out of 5 average rating, 37 reviews

Home away from home, Updated 3 bedroom 2 bath

Immaculate newly appointed, 3 bedroom, 2 bath home comfortably accommodates 6. Air-conditioned bedroom with queen-size sleigh bed, new mattress and bedroom furniture and antiques. Remodeled bath with granite countertop and vessel sink. Dining room seats 6. The kitchen has everything needed to prepare meals. Large dedicated office. .Living area with flat-screen TV, gas fireplace, new leather seating. Upstairs air-conditioned master suite and guest bedroom with newly renovated bathroom.

Top guest favorite

The image captures a scenic view of Bar Harbor, featuring rolling green hills in the background. The harbor is dotted with boats gently floating on calm waters. Coastal buildings align the waterfront, reflecting a charming village atmosphere under a clear blue sky.

Home in Bar Harbor

4.98 out of 5 average rating, 111 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.

Top guest favorite

The front exterior of the cottage features a welcoming entrance with a path of bricks leading to wooden double doors. Lush greenery surrounds the property, and flowerpots add a touch of color to the landscape. Tall trees create a natural border, enhancing the secluded feel.

Home in Bar Harbor

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.

Guest favorite

The open living area is highlighted by a large area rug featuring a geometric pattern. A cozy leather sofa is positioned next to a glass coffee table. Natural light filters in through multiple windows, illuminating a dining space with a wooden table and chairs.

Home in Ellsworth

4.94 out of 5 average rating, 104 reviews

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.

Superhost

A cozy seating area features a beige sofa adorned with patterned throw pillows and a rustic wooden coffee table. A blue armchair provides additional seating. Natural light enters through a nearby window, illuminating the wooden walls and enhancing the warm atmosphere of the space.

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. **

Superhost

A winter landscape features a wide expanse of untouched snow leading to a serene bay. Snow-covered homes dot the shoreline, and trees line the background against a clear blue sky, providing a peaceful view of the water.

Home in Owls Head

4.9 out of 5 average rating, 207 reviews

Comfortable, Close to Town Home, with Oceanview.

This conveniently located home is 1.5 miles from downtown Rockland and all the local festivals. It is a short drive to Camden & Thomaston and only minutes to the Farnsworth Art Museum & Transportation Museum . Centrally located, about 1.5 hours from both Portland and Bangor and only 2 hours from Acadia National Park. Local amenities include, beaches, scenic hiking trails, light houses, lakes, golf, skiing, art galleries, and of course lobsters.

Guest favorite

The front of a two-story house is framed by colorful foliage. The property features a well-maintained yard with flower beds and a welcoming porch. The entrance is accentuated by blue doors and porch lights, presenting a warm invitation to visitors.

Home in Tremont

4.83 out of 5 average rating, 184 reviews

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.

Guest favorite

An outdoor patio area features a large table accompanied by four red chairs. The light blue exterior of the home is highlighted by a window adorned with a planter box, offering a glimpse of greenery. The setting is partially shaded by overhead branches.

Home in Bar Harbor

4.95 out of 5 average rating, 120 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).

Guest favorite

A spacious living room is designed with comfortable seating, featuring a large gray couch and a smaller matching sofa. A coffee table sits atop a decorative rug. Natural light fills the room through multiple windows, offering views of the outdoor space.

Home in Stonington

4.79 out of 5 average rating, 110 reviews

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!

Guest favorite

The open concept living area features a large island with a contrasting wooden base. A wall of windows provides an unobstructed view of the ocean. Neutral-colored cabinetry and light wood flooring complement the space, while dining chairs are positioned around the island.

Home in Lamoine

4.93 out of 5 average rating, 123 reviews

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.