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.

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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, 169 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 living area features large glass doors that allow natural light to flood the space. A unique wooden table with high chairs is positioned next to a modern kitchen, while a cozy seating area includes a chair and decorative accents against a backdrop of greenery.

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.

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, 173 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!

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, 213 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

A charming cottage exterior is displayed, featuring traditional shingled siding and a light blue front door. Two gable dormers top the structure, while flower planters with colorful blooms line the entryway, complemented by clear blue skies overhead.

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

Top guest favorite

A rustic cabin exterior is presented, featuring a wooden porch with two blue Adirondack chairs. A small table with a lantern stands beside the entrance. Surrounding trees provide a natural backdrop, and a flower pot adds a touch of color near the door.

Tiny home in Eastbrook

4.92 out of 5 average rating, 100 reviews

Camp Ottah' Knot Rustic Camping Cabin 2

10 X 12 Rustic Cabins. Two twin beds in each cabin. Each cabin includes two Adirondack Chairs, Firepit, small table, and two chairs indoors, 2 LED powered lanterns and 1 fan, 5 gallons of potable water, simple outdoor kitchen table, a picnic table, propane on demand shower house, The bathroom facility is port-o-Potty shared with the other cabin or a compostable toilet. Both options are available. These are OFF the grid. No power or water in the two cabins.

Top guest favorite

An open living area features a casual seating arrangement with a red accent chair and a blue armchair. A light-colored table sits nearby, complemented by a decorative rug with a lobster design. The kitchen area, equipped with modern appliances, is visible in the background.

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.

Top guest favorite

The log home's exterior features a large, angled window surrounded by tall trees. A wooden deck is visible, and natural stone landscaping with patches of vibrant foliage is present in the foreground, capturing the home's serene connection to the forest.

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 charming guesthouse is displayed, featuring gray shingles and a distinctive cupola atop the roof. Wildflowers bloom in vibrant colors in the foreground, complemented by two large boulders. A garage door is visible, partially open, revealing the interior.

Home in Swans Island

4.91 out of 5 average rating, 100 reviews

Hot Tub Art Sail Loft. Swans Island

Experience the beauty of nature in this art lovers abode. The dynamic brushstrokes and colors create an atmosphere of tranquility, making it an ideal retreat for those seeking inspiration and a connection with nature. Just steps to fisherman’s cooperative with daily catch lobsters. Walk to the lighthouse or lay back in the hot tub after you drink your coffee in the widows walk with harbor views.

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, 477 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.

Top guest favorite

A bright dining area is positioned beside large windows, offering views of the water outside. A wooden table surrounded by four chairs is complemented by a vase of flowers. Natural light floods the space, reflecting off the water and illuminating the warm tones of the decor.

Home in Sullivan

5 out of 5 average rating, 175 reviews

Plovers Cottage, Waterfront

Plovers Cottage on Taunton Bay near Bar Harbor and Acadia Ntl Park provides waterfront living to enjoy swimming, kayaking, and nature up close! Shorefront home with fireplace for cool evenings, spectacular sunset views, all 1linens, kitchen, laundry..... type this in to Youtube search box for arial video! -q9pfaODbcY.