
Waterfront vacation rentals in Winter Harbor
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Quick stats about waterfront rentals in Winter Harbor

Total vacation rentals
Explore 40 vacation rentals in Winter Harbor

Nightly prices starting at
Winter Harbor vacation rentals start at G$10,457 GYD per night before taxes and fees

Verified guest reviews
Over 1,670 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winter Harbor vacation rentals include wi-fi 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!
Top-rated waterfront rentals in Winter Harbor
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Acadia National Park ocean front & garden cottages
Both our houses are designed in the contemporary style. We used custom made decor and cherry tree furniture. A lot of windows, glass doors, bright and open space are inside the house. It is very quiet outside. You most likely will be alone at the beach. We share the whole sea cove with only one neighboring house. It is a pure paradise if you want to live on the beach on your own and within minutes of driving to the main local attractions. You'll be amazed of our botanical garden and landscape.

The Cottage
A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short trail brings you from the cottage to the salt water. We grow organic mixed veggies and fruit, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. Our farm store that is open everyday except Tuesdays, Thursdays and Sundays. The property is 15 minutes away from the Schoodic Section of Acadia and is surronded is by countless hiking trails and access to fresh and salt water.

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.

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!

2026 Summer Waterfront! Hi-Speed Wifi on Flat Bay
Summer 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.

The Boathouse on the ocean
The Boathouse is steps from the ocean. Relax to the sounds and smell of the sea. Watch lobster boats hauling their traps and returning with their catch. Views of Acadia National Park and Mark Island Lighthouse. A true Maine Experience. Walk to the quaint village of Winter Harbor with shops and restaurants. If hiking and biking are your thing, there are trails in the Schoodic section of Acadia National Park. Or just kick back on the sofa and enjoy the views.

*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, and wildlife abounds. Watch the lobster boats work their traps just in front of the house. Not appropriate for small children. Sorry, NO PETS.

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.

Home away from Home
Nestled in a quiet location! Screened in balcony to enjoy the view! Cleared path to the oceanfront to enjoy sun bathing or sea glass hunting Not far from Schoodic Acadis National Park which offers some serene hiking and biking paths Two ferries located in Winter Harbor to go exploring in Bar Harbor There are several fantastic Restaurants I have left plenty of local information at the property

Acadia’s Schoodic Oceanfront Cabin
Enjoy your morning coffee or dinner on the oceanside deck while waves splash underfoot. This home is situated at the mouth of prospect harbor. It’s deck overlooks open ocean with deep water frontage. Take the local ferry to MDI to explore Bar harbor’s restaurants and shops, or stay local and enjoy the less traveled side of Acadia National Park, Schoodic Pennisula (5-10 minute drive).

Sleep next to the ocean in Gouldsboro!
Stay where the ocean will sing you to sleep! This unique 1920's 2 bedroom 1 1/2 bath with a small kitchenette is the perfect place to stay while you enjoy what the Schoodic Peninsula has to offer! We have lots of hiking, biking and kayaking to offer on the Schoodic Peninsula! We also have lots of places to eat including a family friendly restaurant right on site!

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!
Popular amenities for Winter Harbor waterfront rentals
Waterfront apartment rentals

Historic Farm, Waterfront Apartment, Acadia, Pets

Coastal Loft Apartment with Beach Access

Union River Retreat Private Apartment

DTWN Bangor | King Bed | Canal View

Duck Cove Apartment

Oddfellows Hall-Second Floor

Parisian apartment in downtown Belfast, Maine

The American Eagle - Inn on the Harbor
Waterfront house rentals

Waterfront near Acadia | Hot Tub| Kayaks| Bay View

Beautiful Oceanfront Estate

Coveside Lakehouse on Sandy Point

"The Red House" Island Adventure for 6 oceanfront

Water's Edge-Oceanfront with Stellar View

Cabin on the rocks

Magnificent Oceanfront Modern, 8 Guests 4 Bedrooms

Downeast Oceanside Escape
Waterfront condo rentals

Schoodic Escape | Ocean Views | 4BR

Marina side Stern condo

Toddy Haven: A Lakeside Condo Near Acadia.

Cozy 2BR in Downtown Bar Harbor! [Agamont Cottage]

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]
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