
Waterfront holiday rentals in Winter Harbor
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Winter Harbor
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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.

Cozy Cottage on the Penobscot — Panoramic Luxury!
Escape to your private waterfront retreat where tranquility meets luxury. Our Coastal Maine Cottage style home rests on a granite ledge that disappears twice daily with the tide. Enjoy a sun-filled interior with cherry floors, a gourmet kitchen, and a private deck for sunrise coffee or evening wine. Wake to sweeping Penobscot River views & unwind by the fire pit at river’s edge. Just 12 minutes to downtown Bangor, with easy access to urban amenities, Bar Harbor, and Acadia Park. @cozycottageinme

The Maine Getaway - Lakefront with Beach
If you are looking for a place to get away and relax, our house on Molasses Pond may be a good fit for you/your family. It is a hidden gem down a dirt road away from hustle and bustle. Peace and quiet is what you’ll find, along with a gorgeous view. It’s a great place for swimming, kayaking, paddle boarding, grilling, fishing, and laying on the hammock. We try to provide you with all the necessities you may need and are happy to answer any questions. We hope you enjoy it as much as we do!

Belfast Ocean Breeze
Welcome to an exquisite retreat nestled on a tranquil dead-end lane in the thriving coastal town of Belfast. With private access to Belfast City Park and Ocean, this charming space offers unparalleled serenity, and boasting breathtaking views of Penobscot Bay and beyond. The exceptional grounds offer an ideal setting for relaxation with the added allure of explorations along the shoreline or tennis/ pickleball at park/ year round hot tub. Near downtown and Rt. 1. No parties.

"Starry Nights", secluded cottage with ocean views
Soak in spectacular sunsets from this peaceful, secluded cabin overlooking the serene waters of Sawyer's Cove in Blue Hill Bay. Nestled near Seal Cove harbor on the quiet side of Mount Desert Island, this three-bedroom, two-bathroom retreat offers a perfect blend of comfort and natural beauty. Start your day with a cup of coffee or unwind in the afternoon with your favorite drink on the spacious open deck, all while taking in sweeping ocean views that never get old.

*Stunning Views* Oceanfront Chalet w/Fireplace
Oceanfront 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, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS , we're allergic :-(

Graham Lakeview Retreat
Escape to the beauty of coastal Maine in this peaceful and fully-equipped waterfront home—just 40 minutes from Acadia National Park. Enjoy serene water views, launch one of the provided kayaks, or soak in the jacuzzi tub after a day of hiking. Ideal for couples, families, solo travelers, and your four-legged friends, too! Whether you're here for the national park, the coast, or just a quiet escape, this welcoming retreat has everything you need.

The Tiny House with the Enormous View of Acadia
The Tiny House on Goose Cove is the perfect place from which to enjoy your visit to Acadia National Park. Set on three acres of shore front property, the house features spectacular views of Mount Desert Island. The entrance to the Park, and the shops and restaurants of Bar Harbor, are just 20-25 minutes away by car. And when you've had enough of the bustle and crowds, you can retreat to the peace and serenity of this beautiful property.

Beachfront Chalet w/ Gameroom- Decorated For Xmas!
🌅 Welcome To Sunrise Shores Chalet 🌅 Premiere Amenities & Designer Finishes Rivaling Others In The Acadia Region! Experience A Truly Unique Maine Airbnb Fit w/ a Home Movie Theater, 900 Square Foot Arcade/Gameroom, Wood-Burning Beachfront Firepit, and Designer Finishes Curated To Meet The Needs Of Our Guests. 🎅 Ho, Ho Ho...Tis The Season 🎅 Sunrise Shores Chalet Will Be Decorated For The Holidays Through December!

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.

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
Popular amenities for waterfront rentals in Winter Harbor
Waterfront apartment rentals

Canal View|DTWN Bangor|Steps to great Restaurants

Tapley Farm Waterfront Apartment, Acadia, Pets

Union River Retreat Private Apartment

Downtown waterfront Belfast with amazing views.

2 bedroom furnished apartment

Duck Cove Apartment

Oddfellows Hall-Second Floor

Parisian apartment in downtown Belfast, Maine
Waterfront house rentals

Waterfront w/Amazing Views- Central to Acadia

River View | Private Hot Tub | Poplar Treehouse

Vernon's View

Sunny Waterfront Home Overlooking Blueberry Field

Jonesport Water's Edge

Blue Arches: waterfront vacation home on 18+ acres

Downeast Oceanside Escape

Fall & winter retreat on Crockett Cove
Waterfront apartment rentals

Harbor Heights

Marina side Stern condo

Oceanfront Multi-level Condo with Prime Amenities

Toddy Haven: A Lakeside Condo Near Acadia.

2BR Condo + Ocean Views in Downtown SW [Seaglass]

Best views on MDI 2 bdrm 2 bth condo waterfront

Harbor View Cottage Unit A 2 bedroom downtown

Secluded 2BR with Beach Access! [Carriage House]
Quick stats about waterfront rentals in Winter Harbor

Total holiday rentals
Explore 40 holiday rentals in Winter Harbor

Nightly prices starting at
Winter Harbor holiday rentals start at £38 per night before taxes and fees

Verified guest reviews
Over 1,570 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Winter Harbor holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Harbor rentals

4.9 Average rating
Winter Harbor stays are highly rated by guests – averaging 4.9 out of 5!
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- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Sandy Point Beach
- Bear Island Beach
- Sand Beach
- Lighthouse Beach
- Kebo Valley Golf Club
- Spragues Beach
- Wadsworth Cove Beach
- Narrow Place Beach
- Three Island Beach
- Driftwood Beach
- Islesboro Town Beach
- North Point Beach
- Hero Beach
- Billys Shore
- Hunters Beach
- Gilley Beach
- Pebble Beach
- Great Beach
- Cellardoor Winery
- Penobscot Valley Country Club
- Echo Lake Beach




