Family-friendly holiday rentals in Winter Harbor

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)

Bright, Modern Vacation Home w/ Water Views!

Come stay at this serene, cozy, Down East vacation home with expansive water views!  Nestled in the Addison hillside where the Pleasant River meets the sea, this completely renovated getaway offers a modern kitchen & bathroom with brand new appliances, open concept living spaces with water views from every room, and a large deck allowing breathtaking panoramic views of the countryside and skyline.   One hour to Acadia and close to the Bold Coast, Jasper Beach, & Schoodic Point—you can't lose!

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.

Lillebo

Lillebo is set near the end of a dead end road with a five minute walk yielding views over Frenchman's bay with Sorrento in the near view and Winter Harbor and Bar Harbor in the long view. This homey house is set about 200 feet from the road with no neighbors in direct view. There’s a screen porch on one end of the house and a garage on the other. In the garage there is a ping pong table, corn hole, darts and bikes. There are three adult bikes, one youth bike and one kids bike.

Cozy Seal Harbor Cottage

We request anyone who stays on our property be fully vaccinated. Thank you for helping to keep our community healthy! This stand along cottage is on the same property as owner's home and includes 1 parking space. 2 bedrooms with full bath, laundry, and a fully stocked kitchen. House abuts Acadia National Park; Seal Harbor Beach and carriage roads are easy walking or biking distance! Only 12 minutes to Bar Harbor and 5 to Northeast Harbor.

The Tiny House with the Enormous View of Acadia

The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Anchor Down at Schoodic Point

Anchor Down in this nautically inspired salt box home in the quaint seaside town of Winter Harbor, Maine. Comfortably furnished and well equipped for your vacation getaway. At Anchor Down you will be conveniently located across the road from the entrance to Acadia National Park's Schoodic Penninsula with hiking and biking trails and gorgeous views of the ocean.

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!

320 Ft Of Private Beachfront w/ Stargaze Platform!

🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance!