
Waterfront holiday rentals in Winter Harbor
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Top-rated waterfront rentals in Winter Harbor
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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

A-Frame, Hot Tub, Firepit, Oceanfront, Pets
Welcome to your coastal escape! Nestled in nature our cozy and unique A-frame retreat is a haven offering, seclusion, privacy and peaceful views of the ocean. Step into our stylish sanctuary where every detail whispers comfort and charm. Overlooking Little Kennebec Bay Bask in tranquility and enjoy panoramic views of the Little Kennebec Bay from your private deck. ✲ Private Hot Tub! ✲ Outdoor Fire pit! ✲ King Bed! ✲ Abundant hiking! ✲ Wood Burning Indoor Fireplace! ✲ Local Kayaking! ✲ Grill

Timeless Tides Cottage
This comfortable 2 bedroom, one bathroom, A-frame pine cottage is set on its own private point with 350 feet of waterfront! Cook out on the grill, lounge on the deck or dock while taking in the wildlife on a beautiful tidal river. Watch nesting Bald Eagles and Great Blue Herons fishing! There is plenty of sight-seeing in this picturesque area. Rockland is just 10-minutes away where you can enjoy shopping, restaurants, museums, galleries, lighthouses and festivals.

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.

The Maine Salt River Cottage
This waterfront eco-friendly log home, located in an Audubon Important Bird Area and NWF Certified Wildlife Habitat, comfortably accommodates 6 guests. Perched on a bluff overlooking two of Maine's beautiful tidal rivers, it’s home to bald eagles, osprey, and harbor seals and boasts a dazzling night sky and dynamic water views. Salt River Cottage is a proud signatory of the Glasgow Declaration on Climate Action in Tourism.

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

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.
Popular amenities for waterfront rentals in Winter Harbor
Waterfront apartment rentals

Tapley Farm Waterfront Apartment, Acadia, Pets

Union River Retreat Private Apartment

DTWN Bangor | King Bed | Canal View

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 Coastal Retreat 4BR3BA w/ Private Cove

Vernon's View

Cabin on the rocks

Sunny Waterfront Home Overlooking Blueberry Field

Jonesport Water's Edge

Blue Arches: waterfront vacation home on 18+ acres

Downeast Oceanside Escape

Acadia cottage with lobster boat views!
Waterfront apartment rentals

Harbor Heights

Marina side Stern condo

Oceanfront Multi-level Condo with Prime Amenities

Best views on MDI 2 bdrm 2 bth condo waterfront

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

Harbor View Cottage Unit A 2 bedroom downtown

Secluded 2BR with Beach Access! [Carriage House]

Samoset Resort 1br suite, Friday check-in
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 $65 SGD 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
- Rentals with beach access Winter Harbor
- House rentals Winter Harbor
- Rentals with outdoor seating Winter Harbor
- Rentals with a patio Winter Harbor
- Pet-friendly rentals Winter Harbor
- Cottage rentals Winter Harbor
- Family-friendly rentals Winter Harbor
- Rentals with a firepit Winter Harbor
- Rentals with a fireplace Winter Harbor
- Rentals with a washing machine and dryer 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
- Bear Island Beach
- Sand Beach
- Lighthouse Beach
- Kebo Valley Golf Club
- Spragues Beach
- Wadsworth Cove Beach
- Narrow Place Beach
- Driftwood Beach
- Three Island Beach
- North Point Beach
- Islesboro Town Beach
- Hero Beach
- Billys Shore
- Gilley Beach
- Hunters Beach
- Cellardoor Winery
- Penobscot Valley Country Club
- Echo Lake Beach
- Bartlett Maine Estate Winery and Distillery
- Catherine Hill Winery




