Waterfront vacation rentals in Winter Harbor

Bayview Cottage on the Atlantic

Nestled at the head of Pigeon Hill Bay, our cottage is surrounded by 20 acres of fields, marshland, private walking paths, and a private pebble beach on the ocean with views of the Atlantic. Acadia National Park is nearby (1 hour plus) or take the ferry (20 minutes away) to BarHarbor. Acadia Park Schoodic Point is a must see (20 minutes). Enjoy our kayaks, our recommended day trips, blueberry picking, visiting white-tailed deer. For a full week stay we serve a lobster shore dinner for two.

Harborside~Seaglass Beach~Dock~5 min to Acadia

Harborside on Main is a lovingly restored, traditional coastal New Englander cottage located on the hillside above beautiful Southwest Harbor, just 1 mile from Quietside Acadia’s best oceanfront hiking trails. Steps outside the maritime village of SW Harbor with semi-private ocean access, seaglass beach, dock, firepit, and a short walk to all village amenities: the town pier, local bars, restaurants with live outdoor music overlooking the marina, & a private charter on a wooden Friendship sloop.

Magnificent Oceanfront Modern, 8 Guests 4 Bedrooms

Ideally situated at the mouth of Gouldsboro Bay, this modern style gem is awash with ocean views from multiple angles. With an expansive living room and open floor plan, a family or a group can stretch out and enjoy the spacious comforts of this home's contemporary design. A short distance to Acadia National Park on the Schoodic Peninsula, this year round home is an extension of the unspoiled natural beauty that abounds in the region, offering all the amenities for a sublime Maine experience.

Flanders Bay Cabins (Cabin 8 - 2BR)

Located on the Schoodic Scenic Byway in Acadia/Bar Harbor region, our rustic pet-friendly 2BR cabins offer spectacular views. Features include two bedrooms with kitchen and bathroom. Simple, clean accommodations serve as your home base for exploring the beautiful property, shoreline and the bounties of our scenic local region. All cabins come equipped with basic provisions for a comfortable stay. Leave the distractions of modern day behind as you return to the way vacations were meant to be.

Captain Guptill House views of Acadia & lighthouse

Captain Guptill House overlooks Frenchman Bay, with views of Acadia National Park Schoodic and Mark Island Lighthouse. Watch the lobster boats haul their traps and return with their catch. Relax on your front porch, stargazing or just breathing in the ocean air. Walk 1/2 mile up to the Village of Winter Harbor with it's quaint shops and restaurants. If hiking, biking or walking is your thing, the Park has miles of trails. Or do what people come to Maine to do - eat lobster fresh off the boat.

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.

Little Gem - Ocean Cottage near Schoodic & Acadia

Little Gem is a bright and cozy cottage at the intersection of the shore and a stream, with views of offshore islands at the mouth of Gouldsboro Bay. We offer a great base for your Downeast adventures like whale watches, puffin cruises, and kayak trips. Close to Schoodic Loop Road and 60 minutes from Bar Harbor. We offer a comprehensive digital welcome guide to connect you with the best food, adventures, hiking, swimming, and more. Find us on social media as "Maine Coastal Magic".

Acadia Historic Home with Hot Tub and Game Room

✔ This Historic Home Was The Island's General Store & Butcher Shop, Dating Back To 1856 ✔ 5 min to Acadia National Park ✔ Somes Sound Brook In Your Backyard ✔ 7-Person Hot Tub Under String Lights ✔ Kayaking & Swimming In Somes Sound, Long Pond & Echo Lake ✔ Fire Pit, Grill, & Lobster Pot ✔ Game Room with AirHockey, ShuffleBoard, & a SMART TV ✔ Theater With Real Reclining Theater Seats & Movie Candy Provided ✔ All Dogs Welcome ✔ Air Conditioning, Fast Wifi, Washer/Dryer

2026 Fall Colors Waterfront on Flat Bay WiFi

Fall 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.

*Stunning Views* Oceanfront Nordic Cabin

Oceanfront Nordic cabin perched on the edge of Dyer Bay surrounded by large cedar and spruce trees. A perfect retreat nestled in a quiet, private neighborhood off the beaten path. This is where you get away from it all, and enjoy proximity to all the best of Downeast. The view is spectacular, the wildlife abounds and the WiFi is fast! Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS.

Great Timbers Retreat Minutes from Schoodic Park

This private newly renovated log home is nestled right next to the ocean front. Radiant floors with all new appliances and granite countertops. Spa showers in both bathrooms. One large bedroom with king bed and two Queen luxury futon beds for guest. Stone fireplace. Brand new washer and dryer. Charcoal grill outside and picnic table with ocean views. Pet Friendly there are pet beds and crate available

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.