Kid-friendly holiday 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.

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.

Waterfront Getaway on the coast of Maine.

Cozy waterfront, two bedroom apartment with separate entrance and private deck overlooking the beautiful Maine coast. Walk the shore path through a field, filled with wildflowers, to a private cove on the Bagaduce River. The light filled apartment is located above the garage of a restored antique farmhouse and has beautiful water views from the living room and private deck. The perfect spot for a relaxing vacation on the coast of Maine.

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!

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!