Waterfront holiday rentals in Winter Harbor

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Popular amenities for Winter Harbor waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Apartment in Tremont
5 out of 5 average rating, 33 reviews

Adi’s Mountain View

HaydenRating, 5 stars4 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 favourite
Apartment in Bangor
4.86 out of 5 average rating, 110 reviews

Canal View|DTWN Bangor|Steps to great Restaurants

KristenRating, 5 stars6 days ago
Fantastic! Highly recommend this wonderful place. Right in the heart of downtown with plenty to do and see. Loved the modern touch on old charm!
Guest favourite
Apartment in Harrington
5 out of 5 average rating, 9 reviews

Beautiful Waterfront Home Close to Trails & Acadia

HollyRating, 5 stars2 weeks ago
The experience left nothing to be desired as we were looking for a remote spot and a place comfortable and spacious enough to stay inside during bad weather and Jeff’s place checked the boxes. We were the only ones in the 2 unit home. The view is very pretty and the wildlife is plentiful. The access to the water is down a dirt embankment which leads to mud flats at low tide. Beware of the tides if you can get the kayaks down there.
Guest favourite
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 favourite
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 favourite
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 favourite
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 favourite
Apartment in Sedgwick
4.91 out of 5 average rating, 238 reviews

Private Apartment at Cabin Cove

RoryRating, 5 stars3 days 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.

Waterfront house rentals

Guest favourite
Home in Gouldsboro
4.9 out of 5 average rating, 29 reviews

Waterfront Coastal Retreat 4BR3BA w/ Private Cove

MichelleRating, 5 stars11 months ago
We enjoyed our stay at Ashleys's home. It is a beautiful, peaceful and lovely location, with great proximity to Acadia National Park, Winter Harbor and the Schoodic Institute. Our family enjoyed watching the lobster boats in the morning and noodling around the peninsula. It was a very comfortable space, with a well stocked kitchen and dining area.
Guest favourite
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 favourite
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 favourite
Home in Gouldsboro
5 out of 5 average rating, 25 reviews

Oceanfront Acadia Getaway

LaurenRating, 5 stars5 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.
Superhost
Home in Milbridge
4.92 out of 5 average rating, 24 reviews

Oceanfront Cottage on Private Island

SeanRating, 5 stars10 months ago
Great private spot. Off the beaten path. Could be further from Bar Harbor than some might prefer. Very clean, scenery was great and we paddle boarded and kayaked as we had direct access to the water. We really enjoyed our stay and Chad was super responsive and very helpful.
Guest favourite
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 favourite
Home in Jonesport
5 out of 5 average rating, 13 reviews

Saltair, a Downeast jewel

LisaRating, 5 stars8 months ago
What can I say about Salt Air, other than SPECTACULAR! This is one of the most beautiful places I’ve ever stayed. The house is pristine and spotless and the location is beyond beautiful. Mark is an amazing host, he goes above and beyond in communication and in providing such a lovely home to stay in. We were looking for peace and tranquility and we found it in spades here. I could go on for days about how perfect this place is, but instead of listening to me, you should just book your trip to come here! You certainly won’t regret a single moment! Thank you Mark!
Guest favourite
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.

Waterfront condo accommodation

Top Guest favourite
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 favourite
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💖✨️
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
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 favourite
Condo in Orland
4.99 out of 5 average rating, 67 reviews

Toddy Haven: A Lakeside Condo Near Acadia.

KenRating, 5 stars4 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
Condo in Southwest Harbor
4.87 out of 5 average rating, 106 reviews

2BR Condo Downtown SWH + Ocean Views [Driftwood]

VeronicaRating, 5 stars3 days ago
Patrick's place was a great stay for my friends and I. We stayed at southwest harbor and went for hiking in Acadia national park. It is close enough to visit the park as well as bar harbor. The place was very comfortable and clean and we had a good time, drinking coffee in the balcony overlooking the water and cooked dinner another night we decided to stay in. The rooms and bathrooms were very clean and organized and the house was very spacious. Patrick was great at responding to messages and providing instructions. One thing that I would point out is that there is some noise from the road that you can hear in the rooms and some noise from people upstairs walking heavily. However, the hosts had kindly provided earplugs and if you are a heavy sleeper that noise will not be very bothersome. Overall, it was a great stay and I would choose to stay there again. The town of southwest harbor is also super close with cute little restaurants and bakeries, so everything you need is close by.
Guest favourite
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!
Superhost
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.

Quick stats about waterfront rentals in Winter Harbor

  • Total rentals

    30 properties

  • Nightly prices starting at

    $83 NZD 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

Destinations to explore