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.

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Top guest favourite
The rustic cottage features a charming wooden exterior with a sloped roof, surrounded by lush greenery and colorful flowers. Large windows allow natural light to fill the space. The entryway leads to a welcoming atmosphere, complemented by ample outdoor seating nearby.
Cottage in Gouldsboro
4.93 out of 5 average rating, 214 reviews

The Cottage

A rustic cottage in the middle of Darthia Farm. The farm sits along the shore of West Bay and a short walking trail brings you from the cottage to the salt water. We grow organic mixed vegetables, herbs and flowers, raise sheep, ducks, chickens, pigs, and work with Haflinger horses. We have a farm store that is open everyday except Tuesdays 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 water.

Guest favourite
A lakeside view showcases a cottage surrounded by tall trees, with a wooden deck featuring large windows. Colorful kayaks and a canoe rest on the shore near a sandy waterfront, reflecting the serenity of the calm water.
Cottage in Ellsworth
4.88 out of 5 average rating, 108 reviews

Peaceful Branch Lake Cabin minutes to Acadia

Ellsworth is the gateway to Downeast Maine. Just minutes from Acadia National Park, and Bar Harbor, enjoy relaxing along Ellsworth's pristine 9 mile long 120 foot deep Branch Lake (one of Maine's most best kept secrets)! Our furnished lake side cottage is a perfect place to vacation in Maine. You won't find a more beautiful or convenient, yet secluded spot, anywhere. Enjoy using our kayaks, pedal boat, fishing equipment, and canoe. Go swimming in our sandy waterfront or just relax on shore.

Top guest favourite
The A-frame cabin is nestled among trees, surrounded by nature. An inviting view of Little Kennebec Bay is visible in the background, showcasing tranquil waters and coastal landscapes. The private deck with a hot tub extends from the cabin, offering a peaceful outdoor area.
Cabin in Machiasport
4.97 out of 5 average rating, 199 reviews

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

Top guest favourite
Aerial view of a charming cottage surrounded by lush greenery and water. A spacious rooftop deck offers panoramic views. The landscape includes rocky cliffs and forested areas, while a winding bike path is seen in the distance, highlighting proximity to outdoor activities.
Cottage in Gouldsboro
4.97 out of 5 average rating, 101 reviews

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.

Guest favourite
Home in Stonington
4.92 out of 5 average rating, 118 reviews

Bayview House 1br 2ba Stunning Harbor Views

Do you crave balmy summer evenings or frosty winter days that make you feel like you've been transported back to a simpler time? Or long for days spent on the water or experiencing village life with friendly locals in charming pubs tasting local eats? Experience the simple joys of life with rustic yet modern amenities offered at this coastal 2-story home. Whether daily strolls by the water or taking in the sunset on your deck, you'll fall in love with this lovely New England destination.

Top guest favourite
A game of Connect Four is positioned on a woven placemat, set against a backdrop of large windows. The serene view displays the water of Flat Bay and surrounding trees, illuminated by golden sunlight from the setting sun.
Cottage in Milbridge
4.96 out of 5 average rating, 228 reviews

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.

Top guest favourite
A charming cottage is presented beside a serene bay, framed by a colorful display of blooming yellow daffodils in the foreground. The structure features large windows, inviting natural light, and a clear view of the water and distant trees.
Cottage in Sullivan
4.98 out of 5 average rating, 104 reviews

Gordon Cottage on Flanders Bay

Relax with the family at this peaceful and private cottage on the shores of Flanders Bay with views of Cadillac Mountain. Enjoy the expansive lawn and shore access for all of your favorite activities. Bring your kayaks and SUPs. You will not tire of watching the wildlife or water views from this oasis. If you can tear yourself away from the splendor outside your door, Acadia National Park, Mount Desert Island and the scenic Schoodic Peninsula are just 30 minutes away.

Top guest favourite
The image captures the rocky shoreline at sunset, with vibrant shades of purple and orange reflected on the water's surface. To the right, the cabin's A-frame design is highlighted, featuring large windows that offer a view of the surrounding trees.
Cabin in Steuben
4.97 out of 5 average rating, 210 reviews

*Stunning Views* Oceanfront Nordic House

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, we're allergic :-(

Top guest favourite
A modern tiny house features large glass doors opening to a spacious wooden deck. Adirondack chairs are placed near a table under a black umbrella, surrounded by flower pots filled with colorful blooms. Lush greenery is visible in the background, framed by a partly cloudy sky.
Tiny home in Trenton
5 out of 5 average rating, 218 reviews

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.

Top guest favourite
The log home's exterior features a large, angled window surrounded by tall trees. A wooden deck is visible, and natural stone landscaping with patches of vibrant foliage is present in the foreground, capturing the home's serene connection to the forest.
Chalet in Gouldsboro
4.94 out of 5 average rating, 348 reviews

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

Top guest favourite
A view from above captures the cottage set amidst a grassy area, surrounded by trees. In the background, the ocean extends towards the horizon, with hints of shoreline visible. The structure is positioned to showcase its proximity to nature.
Cottage in Lamoine
4.97 out of 5 average rating, 125 reviews

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.

Top guest favourite
A serene sleeping area features a spacious bed adorned with neutral-toned bedding. Two bedside tables are positioned beside the bed, each with a lamp. A wooden bench is placed at the foot of the bed, and a seating area with a chair and small bookshelf is visible in the corner.
Guest house in Franklin
5 out of 5 average rating, 115 reviews

The Spot - Water Views

Off the beaten path in a small quiet town right on the banks of Taunton Bay, enjoy peaceful relaxing location and watch the tide roll in and out. Wake up to waterviews from your bed. You have the entire "Spot" to yourself and whatever wildlife happens to show up that day! ***Shoulder Season is upon us and this is a great opportunity to experience Downeast Maine and all of Acadia with less crowds!

Popular amenities for waterfront rentals in Winter Harbor

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 1,670 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!