Kid-friendly vacation rentals in Winter Harbor

Maine Wilderness Oasis: Hike Swim Kayak Fish

Take it easy at this unique getaway. Spend your days hiking the backyard trails (25 acres behind the house!), swimming or paddle boarding on the lake with a private dock (lake is a 2 minute walk down the driveway!), or traveling to near by coastal towns like Bar Harbor (Bucksport was voted #1 small coastal town in USA!). For dinner, stop by one of the lobster shacks just down the road to bring home your fresh Maine lobster! Come and disconnect (or stay connected if you’re working remotely!).

617 Bayside

Relax with the whole family at this peaceful oceanfront home! Bring your canoe, kayak, or paddle board, and explore the Union River and Union River Bay. Renting kayaks to be delivered to the home is also an option. You’ll enjoy grilling, sitting around the fire pit, and star gazing in the large backyard. This home offers a 1st floor bedroom with king size bed. Upstairs there is a bedroom with a king bed, and a bedroom with a queen. The kitchen and dining room flow through to the living room.

Red Finn@ Acadia National Park

Entire charming 2-bedroom Cottage/Guest house on MDI with air-conditioning, minutes to Acadia National Park & Bar Harbor A prime location in Southwest Harbor that offers the rare combination of a peaceful neighborhood. Quick 2 minutes drive to Eco lake and Eco Beach. Withing 3 minutes to Coffee shops, supermarket, restaurants, bars and shops. This unique family home sits on a gorgeous and well maintained yard with back and front lawn that features a mixture or shrubs, trees and flowers.

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.

Newly renovated cottage in the heart of Downeast

The Woodlands is tucked away on a quiet street off Route 1, minutes from downtown Ellsworth. Newly renovated in 2021, this delightful one bedroom, 2 bathroom cottage has new appliances, including a gas range and washer and dryer, along with all the thoughtful amenities you'll need for a relaxing retreat. With central access to Acadia National Park and all your coastal adventures, the Woodlands is a perfect destination for a peaceful getaway in the heart of Downeast Maine.

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!

A Cozy Little Carriage House *Spectacular Sunsets*

Spectacular view from the private deck: Welcome to the "Rockbound Carriage House" in the quaint town of Brooklin Maine. A cozy 1 Bedroom 1 Bathroom country space with a private deck located next to the historic Rockbound Chapel with breath taking views of the Eggemoggin Reach. A 20 min scenic ride to the town of Blue Hill, 45min to the Acadia National Park, 1hr to Bar Harbor or Bangor. YMMV

Island Getaway - 4BR House (Ocean Views)

★ You will be walking distance from downtown Stonington where you can enjoy local shops, artwork and immerse yourself in the island community. A delightful in-town home with views of Stonington Harbor! The property has a large yard with minimal traffic, perfect for families or a friends getaway. ★ Complementary Kayaks Rentals when you stay 3 nights or more!