Waterfront vacation rentals in Winter Harbor

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Popular amenities for Winter Harbor waterfront rentals

Waterfront apartment rentals

Top guest favorite
The exterior showcases a newly renovated apartment with a wooden deck and fire pit surrounded by natural greenery. Two adirondack chairs stand invitingly by the fire pit, and a private entrance is visible, accented by a rich blue exterior and warm door.
Apartment in Tremont
5 out of 5 average rating, 33 reviews

Adi’s Mountain View

HaydenRating, 5 stars2 days ago
This home is fantastic. it is in such a beautiful and serene setting. you get to watch the sunrises over the mountains in the back, and the outdoor shower is so amazing. inside is comfy and the bed was huge! great hosts as well. very attentive and helping.
Guest favorite
A bright, spacious room features large windows with flowing dark curtains, allowing natural light to illuminate the hardwood flooring. A plush bed is positioned centrally with wooden bedside tables on either side. A wall-mounted television is visible above a compact fridge, enhancing the practical layout.
Apartment in Bangor
4.86 out of 5 average rating, 109 reviews

Canal View|DTWN Bangor|Steps to great Restaurants

ColleenRating, 5 stars2 weeks ago
If visiting Bangor , again, I would stay at the Phenix
Guest favorite
A serene waterfront view features calm waters reflecting the sky, with boats docked along the shoreline. Trees in autumn hues frame the scene, while a pathway winds through the park, leading towards the water and inviting outdoor activities.
Apartment in Belfast
4.86 out of 5 average rating, 105 reviews

Downtown waterfront Belfast with amazing views.

MaddieRating, 5 stars8 months ago
Absolutely beautiful place to stay! Would love to come back :)
Guest favorite
The living room features a blue couch positioned in front of a wall-mounted television. A large window allows natural light to enter, adorned with a light-filtering shade. A cozy chair and a rug with intricate patterns enhance the space, complemented by decorative wall accents.
Apartment in Bucksport
4.93 out of 5 average rating, 42 reviews

Penthouse Dynamic Water Views

DerekRating, 5 stars8 months ago
We had a great stay at the Penthouse! It was a perfect launching point for our downeast adventures in Acadia and points beyond. There was a beautiful waterfront view in a charming small town. The space was cozy, clean, modern and very comfortable for our stay. Highly recommend it.
Top guest favorite
Large windows frame a scenic view of the waterfront, with the ocean visible in the distance. The window area is adorned with a colorful valance, adding a touch of charm. Natural light floods the room, creating a bright and airy atmosphere.
Apartment in Tremont
5 out of 5 average rating, 168 reviews

Duck Cove Apartment

SarahRating, 5 stars1 week ago
Beautiful place! Felt like home away from home. Very clean and has all the essentials you might need for a vacation. Nancy and her husband were very friendly. Highly recommend!
Guest favorite
A private deck is shown, featuring a small table and two chairs, overlooking a harbor scene. Boats can be seen in the distance against a backdrop of clouds and blue sky, creating a serene coastal atmosphere.
Apartment in Stonington
4.94 out of 5 average rating, 108 reviews

The American Eagle - Inn on the Harbor

LeslieRating, 5 stars1 month ago
So peaceful but off season. So not sure how it would be with lots of traffic and people. But the private deck and entrance was wonderful. The water view couldn’t have been more up close and personal with the beautiful harbor. The place was clean and cozy. Perfect lighting. Didn’t watch tv once. A convenient common room for extra supplies or a cup of coffee. Staff was very friendly when we were checking out. No front desk attendant and none needed. They answer messages quickly!
Top guest favorite
A bright bedroom is filled with natural light from a large window, featuring a cozy bed covered with a patterned quilt. An octagonal window provides an additional source of light, while a bedside lamp offers soft illumination. A small green nightstand holds books and a decorative plant.
Apartment in Sedgwick
4.91 out of 5 average rating, 238 reviews

Private Apartment at Cabin Cove

RoryRating, 5 stars1 day ago
A lovely, clean, cozy option that’s convenient to LDI, Brooklin, etc. Nancy is a wonderful host, and the place is quiet and peaceful.
Guest favorite
A panoramic view of the harbor is seen at dawn, showcasing a tranquil sea reflecting the soft colors of the sunrise. Boats are anchored and gently bobbing on the water, framed by silhouettes of trees and distant land. The sky transitions from deep blue to warm oranges and yellows.
Apartment in Southwest Harbor
4.91 out of 5 average rating, 149 reviews

On the water. Walk to Southwest Harbor

AlisonRating, 5 stars7 months ago
Will Definitely Stay Again on Next Trip! What an amazing stay right at a working marina where you have water views on 2 sides and can enjoy watching the inner workings of the life on the many lobster boats leaving every morning and returning at evening. The location was perfect for great restaurants, local shopping, and as a home base for all the hiking destinations. Arcadia Sailing is right there also; our sunset sail was picture perfect. The AirBnB was everything we had read about and hoped for. Parking was great, access convenient, the views of the harbor amazing. As met as a family from NC, TX and OH to cheer my daughter on in the MDI half-marathon. The living area was warm and comfortable, the kitchen well appointed, the bedrooms roomy with great beds and bathroom access. Everything was clean and tidy. Having a washer and dryer was a nice amenity. Molly was available to answer questions and make recommendations. The only negative was that our collective stay was too short!

Waterfront house rentals

Guest favorite
A modern kitchen features sleek black countertops and stainless steel appliances, including a refrigerator and stove. The space includes wooden bar stools at the island. Natural light floods the area, highlighted by a rustic brick column and stylish pendant lighting.
Home in Jonesboro
4.93 out of 5 average rating, 134 reviews

The Chandler House with private waterfront.

AprilRating, 5 stars2 weeks ago
The property was serene and relaxing. It was a much needed space to spend time with nature. The house was adorable. Linens were clean, blankets were cozy, temp works in the house. We plan to book again whenever we are back in the area.
Guest favorite
A cozy waterfront home is set against a backdrop of lush greenery. A spacious deck spans across the front, leading to a circular fire pit area surrounded by Adirondack chairs, inviting relaxation and outdoor gatherings.
Home in Franklin
4.96 out of 5 average rating, 105 reviews

4-Season 3BR Waterfront Oasis with Hot Tub

ChristenRating, 5 stars2 weeks ago
Sydney’s house was perfect for our family! It was clean, with beautiful views on a quiet, private street. The house had plenty of toiletries, we didn’t need to buy any household items while there. The hot tub was clean and perfect for a breezy afternoon looking out at the water. Sydney was a great host, providing tons of recommendations on places to dine and sites to see. Perfect location to visit both the Schoodic Peninsula and Acadia National Park/Bar Harbor! Would love to stay here again.
Top guest favorite
A vibrant sunset paints the sky with shades of orange and pink, reflecting on the calm waters of Brewer Lake. Dark silhouettes of trees frame the foreground, creating a serene and picturesque landscape at dusk.
Home in Holden
5 out of 5 average rating, 32 reviews

Sunset Retreat on Brewer Lake

SarahRating, 5 stars1 day ago
10/10 would recommend Dana’s place! Easy to get to, and absolutely spotless! There is a nice walking trail to the lake to enjoy time by the water. We had a great stay, plenty to do within an hour radius of the Airbnb. As a chicken lover, I adored the flock that roamed the property. They’re very friendly :)
Top guest favorite
An aerial view captures a cozy oceanfront home nestled among trees, with a set of stairs leading down to a rocky shoreline. The tranquil water reflects the surrounding landscape, creating a peaceful setting. Additional seating is visible along the shore, inviting exploration.
Home in Gouldsboro
5 out of 5 average rating, 24 reviews

Oceanfront Acadia Getaway

LaurenRating, 5 stars3 days ago
Mandy was friendly and responsive from the time I expressed interest in the property through checkout. The house and property are spacious and the views of the water are spectacular. The kitchen is well appointed, plenty of room for our family if 5 to spread out, and steam shower was a true bonus upgrade.
Guest favorite
A two-story house is nestled among greenery, featuring a combination of blue siding and white trim. Large windows provide ample natural light, while multiple decks extend the living space outdoors. The serene landscape includes trees and a grassy area, creating a peaceful retreat.
Home in Gouldsboro
4.92 out of 5 average rating, 61 reviews

Enchanting waterfront home on serene 15 acres

JoeRating, 5 stars3 weeks ago
Beautiful place with everything you need for a low key getaway. Not a bad drive to Bar Harbor and Acadia but with better peace and quiet in the mornings and evenings! Definitely would recommend
Guest favorite
Home in Harrington
4.96 out of 5 average rating, 76 reviews

Pines and Tides of Maine.

DahliaRating, 5 stars3 weeks ago
Beautiful place! Can't wait to visit again. Very comfortable and access to nature right in your backyard.
Guest favorite
A picnic table is positioned on a grassy area under a shaded umbrella, facing a serene pond. Nearby, a hammock is gently swaying between two trees, inviting relaxation. The calm water reflects the surrounding trees and clear blue sky, creating a peaceful outdoor scene.
Home in Sullivan
4.95 out of 5 average rating, 19 reviews

Down East Maine Beach Front Escape Near Bar Harbor

MardiRating, 5 stars1 week ago
We loved staying at this lake house. The kayaks were an added bonus that my husband and kids enjoyed. One of the neighbors even gave us a boat ride on the pond to the floating slide and the kids had a blast jumping off of it. The boys caught lots of fish right off shore. It was a great place to stay away from the city on our vacation.
Guest favorite
Home in Hancock
4.97 out of 5 average rating, 38 reviews

Private Oceanfront Home: Hot tub, Games, Fire pit

AmyRating, 5 stars1 week ago
This house was amazing—hosts really have thought of everything when it comes to guest experience! Kayaking out to the tiny islands in the bay a couple times allowed us to see horseshoe crabs and bald eagles up close. The fire pit was great and the “s’mores station” with supplies in the kitchen upon arrival was so cute and thoughtful. Our three kids loved this place and didn’t want to leave at the end of the week. Our boys especially loved the lower level game room with ping-pong, arcade games, and pop-a-shot. The kids also loved reading on the sofa in the upstairs loft overlooking the kitchen. The kitchen is well stocked and we cooked dinner there a couple times during the week. The hosts gave great local recommendations as well—the craft beer at Fogtown Brewing in Ellsworth (less than 15-min. drive) is excellent, and it is very kid-friendly with a large outdoor eating area and wood-fired pizza. We’d love to return to this house! Mosquitoes are fierce so bring bug repellent.

Waterfront condo rentals

Top guest favorite
An open concept space features a modern kitchen with light wood paneling and sleek stainless-steel appliances. A multi-colored granite countertop serves as a dining area with four teal stools. Visible in the background is a cozy seating area and an entry to a bedroom.
Condo in Belfast
5 out of 5 average rating, 17 reviews

Harbor View Cottage Unit A 2 bedroom downtown

BrandonRating, 5 stars9 months ago
What a beautiful location and house. There’s nothing better than sitting in the living room or front porch and being able to see the Belfast Bay. The house is very clean and neat. Beds are comfortable, shower is very hot. Don’t miss the sunrise in the mornings. Overall this is one of our favorite places we have stayed in Belfast.
Top guest favorite
The living room features a spacious layout with high wooden beams accenting the ceiling. A light-colored sofa and a circular coffee table sit on a soft area rug, while large windows provide natural light and a view of the trees outside. A staircase is visible, leading to the upper level.
Condo in Tremont
5 out of 5 average rating, 17 reviews

Secluded 2BR with Beach Access! [Carriage House]

KendraRating, 5 stars2 weeks ago
Patrick's place was exactly as described. We'll appointed. It was in a private and serene location. Views of the ocean from the deck and windows facing the ocean were spectacular! Patrick was extremely responsive from booking through departure. Would definitely recommend this location to anyone not wanting the hustle and bustle of the Bar Harbor area. Utterly enjoyed our stay💖✨️
A serene view of Frenchman's Bay is captured in the image, featuring a boat gently gliding across the water. Lush greenery borders the scene, enhancing the tranquil atmosphere, while a clear blue sky stretches overhead.
Condo in Winter Harbor
4.5 out of 5 average rating, 38 reviews

Harbor Heights

KatonRating, 5 stars8 months ago
Great home in a great location. Very spacious and clean and Corey was very responsive. We had 0 problems with there being a restaurant down stairs. Beautiful views of the bay and a near by field where we watched little kittens playing with each other! It was adorable. We slept great and felt right at home!
Superhost
A rustic building with wooden siding and a wide balcony is shown. Hanging floral planters add color to the exterior while large windows allow ample natural light. The signage displays the name 'The Cannery,' indicating a dining establishment in an inviting marina setting.
Condo in Southwest Harbor
4.91 out of 5 average rating, 91 reviews

Marina side Stern condo

ShannonRating, 5 stars9 months ago
The photos don't do this place justice. It was spacious and squeaky clean. Beautiful views of the water. For a busy marina it was pretty quiet. During the day there would be people just outside the unit talking but nothing disruptive. Great price for a beautiful place. Only about a 25min drive to Bar Harbor. We would definitely stay here again.
Top guest favorite
The exterior of the lakeside condo is illuminated at dusk, surrounded by tall evergreens. Warm light shines from the windows, offering a welcoming appearance. A gravel path leads to the entrance, bordered by a natural stone wall. The serene setting enhances the peaceful ambiance.
Condo in Orland
4.99 out of 5 average rating, 67 reviews

Toddy Haven: A Lakeside Condo Near Acadia.

KenRating, 5 stars2 days ago
We rented both the Toddy House and Rocky House for a week for our family of 12. The houses were as described and in pristine condition. We loved the fact that they were close together, so the late night group could stay up socializing, while the children could be put to bed without distraction. The Toddy House had a pool table which provided lots of late night entertainment. It also had a large open common area to accommodate our group, and we spent a lot of time on the screened porches. We really liked the access to the water with the dock, the canoes and kayaks, and the super cool fire ring. We are the type of family that asks a lot of questions, and Mark was quick to answer and take care of any questions or issues we had. We spent a great deal of time at Acadia, and while the drive was about 45 minutes to get there, it was not a problem at all. We would definitely return to 3Havens if we decided to take another vacation in this area. Mark and Laurie were excellent hosts.
Superhost
The open living area features a light-coloured sectional sofa positioned beside a coffee table. Large sliding glass doors provide access to the private deck, showcasing views of the harbor. A dining area and kitchen can be seen in the distance.
Condo in Southwest Harbor
4.84 out of 5 average rating, 117 reviews

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

TimothyRating, 5 stars3 weeks ago
Great location and clean. As noted in the description, the walls are thin, but we had no issues. The internet connection is spotty, in case you are planning to do some remote work, but we weren't, and had a great time.
Guest favorite
A tranquil view of Southwest Harbor at sunrise, featuring soft hues of orange and purple in the sky. Silhouettes of boats dot the water, while a tree stands prominently in the foreground. The scene captures the peaceful atmosphere of the harbor.
Condo in Southwest Harbor
5 out of 5 average rating, 13 reviews

Best views on MDI 2 bdrm 2 bth condo waterfront

EnkeRating, 5 stars2 weeks ago
We had a wonderful stay in Ted's place. It has amazing views and the unit is well stocked with all necessities. Highly recommended!

Quick stats about waterfront rentals in Winter Harbor

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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