Pet-friendly holiday 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!

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.

The Maine Getaway - Lakefront with Beach

If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

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.

Artsy Tiny House & Cedar Sauna

Our family is excited to share our tiny house with you! Located on our artist collective farm, this is our favorite place on earth. It’s off grid, cottage core, and has a beautiful & fragrant cedar sauna. We are 27 minutes from Acadia National Park and surrounded by truly gorgeous local beaches. We offer super comfy beds, an outdoor shower, twinkle lights, summer nights filled with fireflies, bright maples in the fall, and cozy winter movie nights in a bed alcove like on a boat.

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

Graham Lakeview Retreat

Escape to the beauty of coastal Maine in this peaceful and fully-equipped waterfront home—just 40 minutes from Acadia National Park. Enjoy serene water views, launch one of the provided kayaks, or soak in the jacuzzi tub after a day of hiking. Ideal for couples, families, solo travelers, and your four-legged friends, too! Whether you're here for the national park, the coast, or just a quiet escape, this welcoming retreat has everything you need.

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Welcome to the 'Maine Squeeze'- where morning coffee tastes better on your private waterfront deck and every sunset over Hog Bay feels like a personal show just for you. Located just 40 minutes from Acadia National Park, this cozy coastal retreat offers the perfect blend of adventure and relaxation. Imagine kayaking right from your backyard, soaking in the hot tub under a canopy of stars, and falling asleep to the gentle sounds of the bay.

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.

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

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.