Cottage holiday rentals in Winter Harbor

Acadia Beach shipwreck cottage Bar Harbor

This is Maine coastal living at its best. Enjoy Kayaking, swimming and campfires on your own sand and pebble beach or wait for low tide to find sea stars, crabs, shell fish and more. All new Maine Cabin Master like renovation of 1800s historical beach cottage tastefully appointed with antique features and retro styled appliances and furniture. After exploring nearby Acadia and Bar Harbor, come home to a quiet seaside retreat surrounded by nature and enjoy incredible sunsets over the calm bay.

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short trail brings you from the cottage to the salt water. We grow organic mixed veggies and fruit, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. Our farm store that is open everyday except Tuesdays, Thursdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh and salt water.

Whitetail by the River, Acadia National Park 10m

Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for more Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Stylish ocean-view home on Acadia's Schoodic Loop

This stylish, former 1940s schoolhouse is one of just a few homes located along Acadia's scenic Schoodic Loop; guests can virtually hike or bike by stepping out the back door. Enjoy our crowd-free corner of Acadia or drive 7 min to the ferry for a charming boat ride to Bar Harbor. Alternatively, head up the coast for more hikes, picturesque fishing villages, quirky shops and quintessential Maine culture. At home, enjoy books, original art, a curated record collection and fresh local lobster.

Lamoine Modern Guest House

Relax, recharge, & escape here. A unique & peaceful guest house in the woods of Lamoine, Maine with large windows (without coverings) looking out to the woods. Close enough to Bar Harbor/Acadia National Park (45 min) but removed from the chaos. A 10-minute walk down a gravel road to a beach in Lamoine with distant views of Acadia National Park. Enjoy all weather with our new wood stove fireplace surrounded by large windows. We have a comprehensive guidebook for our guests upon check-in.

2026 Summer Waterfront! Hi-Speed Wifi on Flat Bay

Summer 2026 ~Visit Acadia Park & Bar Harbor by day & stay here at night. Our 1.4 acre shore-front family retreat began an 18 month renovation Fall of 2018 & only opened recently - Dishwasher, new beds, Hi-speed Internet no data limit. We fell in love with this quiet coastal sanctuary, the perfect place to reconnect with nature while staying on grid. ☪ At night you'll experience deafening silence under the natural light of the stars. High-speed Internet keeps you connected.

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.

Gordon Cottage on Flanders Bay

Relax with the family at this peaceful and private cottage on the shores of Flanders Bay with views of Cadillac Mountain. Enjoy the expansive lawn and shore access for all of your favorite activities. Bring your kayaks and SUPs. You will not tire of watching the wildlife or water views from this oasis. If you can tear yourself away from the splendor outside your door, Acadia National Park, Mount Desert Island and the scenic Schoodic Peninsula are just 30 minutes away.

Shore Haven - Oceanfront Home in Corea by the Sea

Peak Season (July & August 2027): Weekly rentals only, Sunday arrival/departure. Enjoy this charming cedar-shingled cottage with 1,850 sq. ft. of single-level living. Features include an open-concept kitchen, dining, living, and sunroom area with spectacular ocean views, 3 bedrooms, 2 baths, and a library off the main bedroom with a double bed. Beautifully landscaped grounds slope gently to 240 feet of dramatic oceanfront.

Meadow Point Cottage

Meadow Point cottage is located on a very quiet five acre property with panoramic views of Frenchman's Bay and Mount Desert Island. It takes about thirty minutes to drive over to MDI and Acadia National Park. The property has a private beach for kayaking and woods with a picnic area and fire pit. It is a wonderful spot for walking and viewing wildlife; ducks, eagles, shore birds, seals and deer.

Quiet lakefront cottage on Graham Lake

Waterfront cottage on quiet Graham lake in the middle of our small working farm. Great spot for quiet relaxation, fishing or kayaking. 2 canoes on the property. Good central location for visiting Bangor, Bar Harbor, Acadia National Park and Downeast Sunrise ATV Trail. Private setting. Wifi available at the farmhouse. Because of family allergies, we cannot host pets

Cottage by Acadia National Park

Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.