
Waterfront holiday rentals in Winter Harbor
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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

Southwest Harbor Cottage
Enjoy unparalleled views of bustling Southwest Harbor and the beauty of Acadia National Park from the comfort of Eagle's Nest. Perched on a granite cliff, this thoughtfully designed little home provides for your every need. For anything else, take the ten minute stroll into the village, where you'll find plenty of local shops and restaurants. You can access the water via a set of stairs leading from the property to the shoreline. End your days on the deck and keep your eyes peeled for seals!

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!

Lake Front-Spa Tub-Fire Pit-Full Kitchen-Canoe
Need to escape the hustle and bustle or a cramped work from home life? The year-round lakehouse is perfect for the outdoor recreational enthusiast, the work-from-home adventurist, a family trip to Acadia, or a cold-weather spa escape. Enjoy this spacious waterfront home in Bucksport, Maine. Relax in the spa tub, fish from the included canoe and kayak, or work remotely with a view. When you want to explore, the home's location is convenient to Bangor, Brewer, Ellsworth, and Bar Harbor!

Water's Edge-Oceanfront with Stellar View
Water’s Edge offers panoramic coastal water views in a 2-Bedroom+Loft, 1-Bath vacation cottage located feet from the shore. Ideally located between Acadia National Park’s Schoodic Peninsula and Mt Desert Island, your serene cottage has private access to the coast with wonderful views of Frechman Bay and Cadillac Mountain. Explore all the beauty of Acadia National Park, climb local mountains, kayak the Mt Desert Narrows or just watch the tides and mountains from your private deck!

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.

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.

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.

320 Ft Of Private Beachfront w/ Stargaze Platform!
🌊 Welcome To Compass Point Cottage 🌊 Placed Below A Winding Driveway At The Edge Of Compass Point, Our Beachfront Cottage Rests 20 Feet From The Water's Edge...Surrounded On Two Sides By Over 320 Feet Of Private Shoreline With Views Of Petit Manan Lighthouse In The Distance! 🎅 Ho, Ho Ho...Tis The Season 🎅 Compass Point Cottage Will Be Decorated For The Holidays Through December!

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

The GrindStone Bungalow

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Coveside Lakehouse on Sandy Point

Vernon's View

Cabin on the rocks

Sunny Waterfront Home Overlooking Blueberry Field

Jonesport Water's Edge

Lake Front-Kayaks-Dock-Fire Pit-Sand Beach-Acadia
Waterfront apartment rentals

Harbor Heights

Marina side Stern condo

Oceanfront Multi-level Condo with Prime Amenities

Toddy Haven: A Lakeside Condo Near Acadia.

Samoset Resort 2br Suite, Saturday Check-In

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
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 € 43 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!
Destinations to explore
- House rentals Winter Harbor
- Pet-friendly rentals Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Rentals with a washing machine and dryer Winter Harbor
- Family-friendly rentals Winter Harbor
- Rentals with beach access Winter Harbor
- Rentals with a firepit Winter Harbor
- Rentals with a fireplace Winter Harbor
- Cottage rentals Winter Harbor
- Rentals with a patio Winter Harbor
- Waterfront rentals Hancock County
- Waterfront rentals Maine
- Waterfront rentals United States
- Acadia National Park
- Northeast Harbour Golf Club
- Acadia National Park Pond
- Sandy Point Beach
- Sand Beach
- Bear Island Beach
- Lighthouse Beach
- Kebo Valley Golf Club
- Wadsworth Cove Beach
- Spragues Beach
- Narrow Place Beach
- Islesboro Town Beach
- Driftwood Beach
- North Point Beach
- Three Island Beach
- Hero Beach
- Billys Shore
- Gilley Beach
- Hunters Beach
- Cellardoor Winery
- Asper Beach
- Penobscot Valley Country Club
- Echo Lake Beach
- Catherine Hill Winery




