Pet-friendly vacation rentals in Winter Harbor

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Winter Harbor

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

A wooden bungalow is situated among snow-covered ground and tall trees, with a slanted roof and turquoise door. A friendly dog rests in the foreground, surrounded by wood shavings. A ramp leads up to the entrance, providing access to the cozy structure.

Farm stay in Franklin

4.91 out of 5 average rating, 566 reviews

Boreal Blueberry Bungalow - Organic Farm Getaway

This sweet bungalow is located on a tucked-away organic farm, 45 minutes from Bar Harbor and Acadia National Park, and directly abutting the Downeast Sunrise Trail and thousands of acres of conservation land. Newly crafted space with pine interior and cork flooring. For folks who appreciate simple living but want a cozy bed! Cot available for third person. Full size mattress, all bedding, stove with oven, pots, pans and dishes, small fridge and sawdust based composting toilet (on back porch)

Guest favorite

A deck overlooks a spacious green lawn surrounded by trees showcasing vibrant fall foliage in shades of orange and yellow. The peaceful outdoor space is ideal for relaxation and enjoying the natural beauty of the landscape.

Home in Gouldsboro

4.93 out of 5 average rating, 171 reviews

The Adventure House

The Adventure House was named by a family of houseguests with 3 fun and lively children who filled their time here with adventures at Acadia National Park and beyond! We are 10 minutes from the quiet side of the park and just under an hour to the busy side, both filled with scenic beauty! We have an added amenity for families traveling with extra family or friends. We're now offering a beautiful camper that comfortably sleeps 6 on the property available only for an extra charge after booking.

Guest favorite

An open interior space features large windows allowing natural light to fill the room and views of the surrounding trees. A rustic wooden dining table is surrounded by high stools, while a cozy chair and a swing hang near a glass door leading to the outdoors.

Home in Gouldsboro

4.94 out of 5 average rating, 219 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.

Guest favorite

A renovated boat is situated outside, serving as a second lounge. Its classic shape features a deep red hull with a contrasting black top. A pathway of cobblestones leads up to a fenced area, while the cottage is visible in the background against a bright sky.

Cottage in Beals

4.98 out of 5 average rating, 125 reviews

Harbor views + stylish interior + boat lounge

Situated in the heart of a small lobster fishing village, Bridge View is a stylish, 3 bedroom cottage with renovated boat lounge. Bridge View is the perfect place to unwind and watch the lobster boats go by. It's also ideal for experiencing Downeast culture up close. Go for a stroll around the fishing village; buy fresh lobster from the docks; hike beautiful Great Wass nature preserve; or just use the house as a base to explore Bar Harbor, the bold coast, Eastport, Campobello and more.

Top guest favorite

A blue cottage stands amid a lush green yard, bordered by mature trees. A well-maintained lawn features a few white chairs placed throughout, along with a simple stone arrangement. The scene is brightened by clear blue skies and abundant sunlight.

Guesthouse in Orland

4.99 out of 5 average rating, 175 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Charming cottage in Orland Village, 2 minutes from Bucksport, a short walk away from the Orland River and its estuary on the Penobscot Bay. Nestled on 3.5 acres of wooded land, 300 ft behind an 18th-century colonial house. Completely self-contained with equipped kitchen. Fast 400 Mbs cable internet/WiFi. 45 minutes to Acadia National Park, 30 min. to Belfast, 20 min. to Castine. Perfect base for hiking, kayaking, sailing, or discovering the maritime past of the area. Pet friendly!

Superhost

The open living area features warm wood floors and ceiling beams, with a cozy sofa draped in a light cover. A dining table is situated near the kitchen, accompanied by a charming light fixture. Shelves filled with books add a touch of character to the space.

Barn in Tremont

4.88 out of 5 average rating, 320 reviews

The Seamist Cottage - Converted Historic Barn

Cozy, fully converted historic barn within easy walking distance to the rocky shore of Bass Harbor, a busy lobstering port. An ideal, pet friendly, home base while exploring Acadia National Park. The Seamist is located on "the quietside" of the island. Six minutes from Southwest Harbor and thirty minutes to Bar Harbor, the Seamist also offers guests private hot tub access! Two guests maximum, not a suitable space for children. Please keep allergies in mind when booking. No smoking.

Top guest favorite

A modern two-story home is framed by trees, featuring a light grey exterior with large windows. A wooden stairway with multiple steps leads to the welcoming entrance, designed for accessibility. The surrounding area is natural and sloped, enhancing the home's integration with the landscape.

Cottage in Milbridge

4.97 out of 5 average rating, 214 reviews

Summer 2025 Waterfront Getaway! Hi-Speed Wi-Fi

Spring 2025 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

Top guest favorite

Home in Bar Harbor

4.99 out of 5 average rating, 202 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! Registration #VR1R25-047

Guest favorite

A modern kitchen is showcased, featuring dark cabinetry and a large central island with a white countertop. Stainless steel appliances, including a refrigerator and oven, are visible. Recessed lighting highlights the space. A cozy living area is seen in the background, complemented by plants.

Guesthouse in Ellsworth

4.86 out of 5 average rating, 149 reviews

Large adorable 1 bedroom loft with ocean frontage

What you will love - Modern living space - Ocean Access - Frontage on Union River - Close to everything - but seems like you are in the woods. - Abundant wildlife - Store within walking distance - Outdoor deck on river - Views of Ellsworth Harbor - Full kitchen and laundry - Full bath and Half bath for guests - Air conditioning - Upscale Contemporary Decor - Situated on a 10 acre lot, with large lawn, pond, and within a 2 minute drive to downtown Ellsworth Maine.

Top guest favorite

Home in Bar Harbor

4.93 out of 5 average rating, 243 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. We are dog friendly, however we do not accept cats for allergic reasons.

Guest favorite

A newly renovated log home is situated amidst tall trees, surrounded by rocky terrain. Large windows reflect the natural light, revealing a spacious porch that invites outdoor relaxation. The architectural design features a steep-pitched roof, harmonizing with the forested landscape.

Chalet in Gouldsboro

4.93 out of 5 average rating, 324 reviews

Great Timbers Retreat Minutes from Schoodic Park

This private newly renovated log home is nestled right next to the ocean front. Radiant floors with all new appliances and granite countertops. Spa showers in both bathrooms. One large bedroom with king bed and two Queen luxury futon beds for guest. Stone fireplace. Brand new washer and dryer. Charcoal grill outside and picnic table with ocean views. Pet Friendly there are pet beds and crate available

Guest favorite

The exterior of a spacious two-story house is presented, featuring a light gray facade with white trim. Three gabled windows adorn the second floor, and an outdoor deck with white railings is visible above ground level.

Apartment in Hancock

4.96 out of 5 average rating, 478 reviews

7 Harbor view Dr

We have an open, airy studio apartment with a queen bed, twin bed, and twin trundle under the twin, private bathroom and full kitchen, located approximately 25 miles, or about a 40 minute drive, from Acadia National Park. Pets are welcome as we have a small fenced in area in the backyard. Bring home a lobster and cook it in the fully furnished kitchen.