Family-friendly vacation rentals in Winter Harbor

Family/Friends Getaway Hidden on Mt Desert Island

Escape to our enchanting woodland retreat on MDI, surrounded by Acadia National Park. Secluded at the end of a dirt road, our home borders the 2000-acre Kitteridge Brook forest. Discover tranquility with 3 miles of private trails right outside your door. Ideal for exploring Acadia's magic, our 3-bedroom home features an open concept kitchen, living, and dining area, along with a spacious deck. Perfect for large families or two small families, experience the ultimate oasis in the heart of nature.

Lakefront Log Cabin on Pleasant Lake

Best view on the Lake! 500' of frontage out on a point. Private boat launch and dock site available. Covered deck to watch the sunset. Outdoor firepit, as well as indoor gas insert. Propane grill on site. Plenty of parking available. In the winter, ideal location for snowmobiling and ice-fishing. Right on to the lake and then 4 locations to get on local/ITS trails. Great fishing 200’ from the porch. Once the ice is out, hit the black crappie and Smallies from the convenience of a private launch

Charming, Family-Friendly Historical In Town Home

STR24-11 Sadler House is an in-town historic home located just blocks from Main Street. We have made it truly convenient for families, with flexible sleeping arrangements in three cozy upstairs bedrooms, two full baths, a fully equipped kitchen, large dining table, living room, and sun room. Walk to shops, restaurants, museums and the harbor in minutes. Our house is the perfect home base for exploring all that the beautiful midcoast has to offer. Ask us about free delivery from Ruckus Donuts!

On the water. Walk to Southwest Harbor

If you want to be near the action of an active and interesting harbor, this is the place for you. You will have a front row seat to spectacular morning sunrises over the harbor, the comings and goings of the fishermen and the many boats docked at the marina and anchored in the harbor. This spacious four bedroom two and a half bath home is located at the Great Harbor Marina just half a mile from downtown Southwest Harbor. Walk to restaurants, art galleries, specialty shops and more.

Hadley Point Hideaway, Quiet & Peaceful

This high-end 2 bedroom bungalow, with loft, is a guest favorite. Airbnb marketed this cottage as one of their most "wish listed" listings in Fall 2024. Hadley Point Hideaway is adjacent to the owners residence and is designed for privacy. This bungalow is nestled in the woods on a desirable road for walking, running & biking. Hadley Point Beach is walking distance from the house. This house is 10 minutes from Bar Harbor and 5 minutes to the Acadia National Park entrance.

The Old Charm of Cozy Victorian(downtown)

Victorian style apt (on 2nd floor) with a lot of charms and a deck. Right in downtown, walkable to everywhere, 5 min to island explorer/bus stop, Village green, library, museum, historical churches, kids playground, many restaurants and more. You’ll love it because of the quiet you rarely find in the busy town and the convenience of the location, which allows you to easily catch a free shuttle bus to anywhere in the park without the hassle of driving and parking.

Pretty Marsh Cottage

This beautiful, light-filled cottage on waterfront property on the western side of Mount Desert Island has picturesque views of the Mount Desert Narrows and access to a private pebble beach. The house is on very secluded wooded property for a nice private getaway. All you will hear are the sounds of birds and waves lapping up on the beach. Just a short drive to all that Acadia National Park has to offer!

Charming Belfast home. Walk downtown/water

Enjoy this charming, well-maintained neighborhood, positioned right between downtown and the town park. This house also sits just a block up from quiet public access to the beach. Walk to everything! Exquisitely landscaped backyard. Lovely historic 1920 roots, with fresh, clean, modern updates. Glimpse water through trees.

Robin's Nest with Water Views

Robin’s Nest is perched at the top of a quiet, dead-end street, less than a mile walking distance to the center of Southwest Harbor. Catch glimpses of harbor views from many rooms in this sweet 2 bedroom, 1 bath home. This home is best suited for families of up to 5 people or groups of up to 4 adults.