Pet-friendly vacation rentals in Winter Harbor

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 800 Mbs fiber 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. We’re very pet friendly!

Flanders Bay Cabins (Cabin 9 - 1BR)

Located on the Schoodic Scenic Byway in Acadia/Bar Harbor region, our rustic pet-friendly 1BR cabins offer spectacular views. Features include one double bed with kitchen and bathroom. Simple, clean accommodations serve as your home base for exploring the beautiful property, shoreline and the bounties of our scenic local region. All cabins come equipped with basic provisions for a comfortable stay. Leave the distractions of modern day behind as you return to the way vacations were meant to be.

Organic Farm Artistic Eco-Loft

We truly want Everyone to feel welcome here! Bar Harbor is a scenic 45 minute drive away. There is great hiking/xc skiing in our huge back yard (Sunrise trail/Maine reserve land) Rustic farm apartment with full kitchen, breakfast foods provided first day. Farm veg can be bought in season & our own wine, jam, hot sauce, maple syrup. Can accommodate 6 folks, one in a cupola! Hot shower & heat. There is a sawdust compost toilet-Easy to use & no smell! We are on Wabanaki land, give all respect.

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.

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.

Quiet 2-bedroom house on Acadia's doorstep.

Minutes from Acadia, Bar Harbor, Ellsworth and other DownEast destinations. Relax with the whole family at this peaceful home in the heart of Vacationland. We are nearing the end of a long renovation, so you will find some projects unfinished (mostly exterior). But, we hope that won't stop you from having a great time exploring the area. New floors, kitchen, lighting, and hot water heat pump - we've poured a lot of love and energy into making this a great spot for our family, and yours!

Edgewater Cabins

Edgewater is centrally located off of Route 1 (Schoodic Scenic By-way) in Sullivan Harbor. You can enjoy our beach and picnic tables on the wharf while surrounded by amazing views. You will find a tennis court just a short walk up our driveway. Nearby there are restaurants and dining, local hiking trails, and Acadia National Park. There are 2 other small cabins plus larger ones available that can accommodate families. In July and August there is a 7 night minimum stay from Sat. to Sat.

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

Unique, Colorful Off-Grid Cabin

Our family is excited to share our off-grid *lite* cabin with you! Located on our artist collective farm, this is our favorite place on earth. It’s bright, beautiful, and filled with color. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, beach cruisers, an outdoor shower, hot tub, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and a cozy wood stove in the winter.

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.

Open Hearth Inn Cottage 12 - 10 min to Acadia!

Cottage 12 is a cozy cottage with one king bed, a full bath with shower, A/C, mini-fridge, cable, television, hairdryer, coffee pot, microwave, cook top, pots and pans. Also, a sleeper sofa, and free Wi-Fi. As with all guests who join our Ohana, there is full access to the indoor kitchen downstairs in the main building, the outdoor kitchen and grill, full access to the common use hot tub, and the bonfire pit on the back lawn.

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