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 view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.

Cottage in Hermon

4.92 out of 5 average rating, 105 reviews

Lakefront Cottage on Tracy Pond, New Hampshire

Lakefront private cottage right on 47 acre Tracy pond. This pond has no public access so it is very quiet with only my home and another Air BnB rental on the 25 acre parcel. Loons, eagle, deer, otter and beaver are around. It has a fully equipped kitchen, deck and gas grill along with a stone firepit. Minutes to Bangor airport and downtown and one hour to Acadia National Park. You can swim and boat on the pond with kayaks and a canoe provided. Pets welcome but keep on leash and clean up after.

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, 550 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

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, 191 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

4.97 out of 5 average rating, 115 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, 156 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, 200 reviews

Spring 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.

Guest favorite

A charming wooden cottage stands elevated on a sturdy foundation, framed by lush greenery. The spacious deck features hanging flower baskets that add vibrant color, while a bicycle rests beside the gravel path leading to the garage underneath.

Tiny home in Hancock

4.97 out of 5 average rating, 148 reviews

Treetop Loft at Crabtree Neck Cottages

Pets negotiable. MUST DISCUSS BEFORE YOU REQUEST. Crate trained pets allowed for a fee. DISCOUNT for over 3 nights or dogs under 12 lbs. Ask! Pets come by prior arrangement only. Treetop sleeps 2, or 3 in a pinch. Must discuss well behaved children 6 or older as the deck is high. Owners/guests use garage/laundry below the studio. Kitchenette includes two burner hot plate and large dorm fridge, coffee maker, microwave, and toaster oven. Rental Agreement, PET POLICY, see notes.

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, 300 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

A spacious living area features a cozy seating arrangement with a neutral-toned sofa and chairs. A coffee table sits at the center, while a large window allows natural light to fill the space, offering a view of the outdoor deck. A dining table and a workspace are also visible.

Home in Bar Harbor

4.91 out of 5 average rating, 100 reviews

2BR Apt + Deck, Fire Pit, Backyard! [Maine Escape]

The Maine Escape is a cozy 2 BR Home located above our garage on the property. The entrance is via the back deck and is secluded from the front of the house providing privacy for the unit. The deck has outdoor furniture as well as a view of Hamilton Pond across the street. Location Highlights: -6 min Drive to Acadia National Park [Hulls Cove Entrance] -12 min Drive to Downtown Bar Harbor

Top guest favorite

The camp exterior features a spacious deck with a screened-in area, softly illuminated by hanging lights. Snow blankets the ground, and a black dog stands in the foreground, observing the surroundings. Surrounding trees offer a natural backdrop.

Cottage in Mariaville

4.97 out of 5 average rating, 108 reviews

Restored camp nestled in the Maine woods

Our little camp is ready for your rest and relaxation on Graham Lake, Maine. Quiet setting, 15 miles from Ellsworth and 24 miles from Mount Desert Island. Great for adventuring to Blue Hill and Schoodic Peninsulas. Escape the island crowds and experience Maine how locals do...upta camp! Lovingly restored and available for limited weeks. Now available for winter bookings!

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, 155 reviews

The Adventure House

Our house was named “The Adventure House” by a family of houseguests with 3 fun and lively children. They told us that their time in Maine was filled with fun adventures so the kids started calling the house “The Adventure House” during their stay. We thought that was fitting as we are so close to Acadia National Park and many other pathways to adventures!

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, 161 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.