Cottage holiday rentals in Winter Harbor

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 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Fall Foliage 2025 Waterfront! Hi-Speed Wifi

Spring 2025 ~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.

Shore Haven - Oceanfront Home in Corea by the Sea

*** Peak season- Jun 14 to Sep 13, 2026- weekly bookings only with arrival/departure on Sunday***. This cedar shingled cottage home boasts 1850 sq ft of living space on one level. It has open concept Kitchen/Dining/Living/Sun room with spectacular ocean views; 3 bedrooms; 2 baths; and a library/reading room with a double bed. The property is nicely landscaped with a gently sloping lawn to 240 ft. of bold 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.

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.

Cliff-perched cottage w private hiking trails

Designed to evoke a ship, this stylish 2BD home overlooks the ocean and is surrounded by 30+ acres of woods, wildlife, and area beaches. 12 of these acres include private hiking tails that wend along the water. Hike, kayak, BBQ, explore Downeast working harbors, or just relax on the deck. Enjoy complete privacy just 17 min from town.

Ellie's Cottage—lovely, bright, and tasteful

This sweet little cottage has amazing light and views across fields and woods into the ocean. Sunrises are spectacular and stargazing at night is awe-inspiring. Perfect for a quiet getaway where you can really unplug. The State Park is just 2 miles away. Roque Bluffs is a special place in the world with much to explore.

Salt Air & Beachfront Breezes 20 Steps To Beach

🌊 Welcome To Rocky Beach Cottage 🌊 Perched On Coastal Waters and Tucked Into The Woods, Our Cottage Sits On 120 Feet Of Private Shoreline For You To Explore. A True Maine Beachfront Cottage Only 20 Minutes Drive to the Quiet Side of Acadia National Park...The Schoodic Peninsula!