Cottage vacation rentals in Winter Harbor

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Top-rated cottage rentals in Winter Harbor

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Top guest favorite
A serene landscape captures the transition of day to night, with the sky filled with shades of purple and pink. Smooth rocks line the water's edge, reflecting the calming colors onto the still surface of the bay. Lush greenery accents the foreground.
Cottage in Milbridge
4.97 out of 5 average rating, 117 reviews

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.

Guest favorite
A fire pit area is surrounded by four Adirondack-style chairs, set on a grassy patch. Views of the harbor and surrounding trees provide a tranquil backdrop, with the cottage’s red exterior visible in the corner of the image. The scene captures a peaceful outdoor gathering space.
Cottage in Southwest Harbor
4.97 out of 5 average rating, 156 reviews

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!

Top guest favorite
A cozy porch is featured at the entrance, highlighted by rustic wooden beams and comfortable seating. Surrounding greenery and distant crops create a serene countryside backdrop, enhancing the peaceful setting of the cottage.
Cottage in Trenton
4.99 out of 5 average rating, 677 reviews

Whitetail by the River, Acadia National Park 10m

Whitetail Cottage - 4 MILES TO MDI- nestled between woods edge & rolling meadows w/views distant views of the Jordan River! Tiny home with WIFI is ONLY 10 MILES to Acadia National Park -a hikers paradise! Minutes to Mount Desert Island but secluded enough to disconnect &get back to nature. Enjoy a stroll to the water, privacy, breathtaking sunsets,stargazing & local wildlife! Perfect for 2 & cozy for 4. Short drive to MDI,Acadia, Bar Harbor,Ellsworth,Southwest Harbor,Shops & Lobster Pound

Top guest favorite
Cottage in Gouldsboro
4.91 out of 5 average rating, 160 reviews

Shore Haven - Oceanfront Home in Corea by the Sea

New gas fireplace insert of fall 2025** Peak season- Jun 14 to Sep 13, 2026- weekly bookings only with arrival/departure on Sunday***. This cedar shingled cottage home boasts 1850 sq ft of living space on one level. It has open concept Kitchen/Dining/Living/Sun room with spectacular ocean views; 3 bedrooms; 2 baths; and a library/reading room with a double bed. The property is nicely landscaped with a gently sloping lawn to 240 ft. of bold oceanfront.

Top guest favorite
The stand-alone cottage is surrounded by lush greenery and trees displaying autumn colors. A small picnic table is seen on the neatly manicured lawn, while a pathway of stone pavers leads to the entrance. The exterior is painted in a calming shade of blue.
Cottage in Mount Desert
4.99 out of 5 average rating, 179 reviews

Cozy Seal Harbor Cottage

We request anyone who stays on our property be fully vaccinated. Thank you for helping to keep our community healthy! This stand along cottage is on the same property as owner's home and includes 1 parking space. 2 bedrooms with full bath, laundry, and a fully stocked kitchen. House abuts Acadia National Park; Seal Harbor Beach and carriage roads are easy walking or biking distance! Only 12 minutes to Bar Harbor and 5 to Northeast Harbor.

Guest favorite
A charming cottage exterior is framed by two trees, featuring a striking red door and black shutters on white siding. Two wooden benches are positioned in front, alongside a picnic table, inviting outdoor gatherings and relaxation.
Cottage in Trenton
4.9 out of 5 average rating, 125 reviews

14 1Br Cottage in Bar Harbor Open Hearth Inn

Cottage 14 is a quaint rustic cottage with one king bed, a full bath with shower, A/C, mini-fridge, cable, television, iron/ironing board, hairdryer, coffee pot, microwave, and free Wi-Fi. As with all guests who join our Ohana, there is full access to the indoor kitchen downstairs in the main building, the outdoor kitchen and grill, full access to the common use hot tub, and the bonfire pit on the back lawn.

Top guest favorite
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, 121 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 favorite
An outdoor seating area features several adirondack chairs arranged around a firepit. A golden sunset casts warm hues over the calm waters, and rocky shorelines are visible in the distance. Sparse trees line the area, completing a serene coastal setting.
Cottage in Gouldsboro
4.99 out of 5 average rating, 197 reviews

Beachfront Christmas Cottage w/ Firepit!

🌊 Welcome To Rocky Beach Cottage 🌊 Perched On Coastal Waters and Tucked Into The Woods, Our Cottage Sits On 120 Feet Of Private Shoreline For You To Explore. A True Maine Beachfront Cottage Only 20 Minutes Drive to the Quiet Side of Acadia National Park...The Schoodic Peninsula! 🎅 Ho, Ho Ho...Tis The Season 🎅 Rocky Beach Cottage Will Be Decorated For The Holidays Through December!

Top guest favorite
A vibrant sunset is reflected on the calm waters of Graham Lake, with streaks of orange, pink, and purple filling the sky. Silhouettes of distant hills and trees frame the scene, creating a serene atmosphere perfect for relaxation.
Cottage in Waltham
4.95 out of 5 average rating, 843 reviews

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

Top guest favorite
A modern kitchen is featured, adorned with wooden cabinets and a countertop. Stainless steel pots and utensils are neatly arranged on the stove. A small dining table is set with a bottle of wine and fresh fruit. Natural light floods the space through a window.
Cottage in Mount Desert
4.98 out of 5 average rating, 478 reviews

Cottage by Acadia National Park

Located by the Giant Slide Trail and bordering Acadia National Park the nature enthusiast will enjoy the comfort and central location of this cottage on Mt. Desert Island. Making touring in Acadia easy with trails, sites, and Bar Harbor within easy access. Walk right from the cottage to access the carriage roads and the Giant Slide Trail which leads up Sargeant Mountain.

Top guest favorite
A serene coastal scene depicts a rocky shoreline at low tide, with gentle waves lapping at the water's edge. Tall trees border the landscape, casting subtle shadows. The clear sky reflects soft light over the calm water, creating a peaceful atmosphere.
Cottage in Gouldsboro
5 out of 5 average rating, 216 reviews

Driftwood Cottage

This is the million dollar view on the Schoodic Peninsula. Sit on your private deck and private beach, sipping wine, while gazing across Frenchman Bay as the sun sets over Cadillac Mountain. Watch lobster boats crisscross the bay while eagles soar overhead.

Top guest favorite
Cottage in Franklin
4.95 out of 5 average rating, 101 reviews

Mainestay Cottage - 4 Season Waterfront Retreat

Welcome to Mainstay Cottage! A private waterfront getaway ideally located between Bar Harbor/Acadia and Schoodic. This cozy, well-stocked home provides ample space to relax and recharge in a quintessential Downeast Maine setting.

Popular amenities for Winter Harbor cottage rentals

Quick stats about cottage rentals in Winter Harbor

  • Total vacation rentals

    Explore 10 vacation rentals in Winter Harbor

  • Nightly prices starting at

    Winter Harbor vacation rentals start at ﺩ.ﺇ881 per night before taxes and fees

  • Verified guest reviews

    Over 460 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winter Harbor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Harbor rentals

  • 5 Average rating

    Winter Harbor stays are highly rated by guests—averaging 5 out of 5!

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