House vacation rentals in Winter Harbor

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Popular amenities for Winter Harbor house rentals

House rentals with a pool

Guest favorite
A clear blue swimming pool sits within a wooden deck, surrounded by lush greenery and a white privacy fence. A shaded seating area features comfortable lounge chairs, inviting relaxation in the sunlit outdoor space.
Home in Bangor
4.97 out of 5 average rating, 309 reviews

Cozy, fun, 3 bedroom home with a pool and Hot Tub.

KaitlynnRating, 5 stars1 week ago
Me and my friends loved this BNB!! The hot tub was amazing and the pool was an awesome addition. Instructions were clear and even called to walk me through everything. Plenty of places to sleep and loads of places to go!
Guest favorite
A 27-foot swimming pool is surrounded by lush greenery, offering a serene outdoor setting. Two lounge chairs are positioned next to the pool, which is framed by a wooden deck and privacy panels. The tranquil atmosphere invites relaxation in nature.
Home in Waltham
4.92 out of 5 average rating, 24 reviews

Higgins Retreat Quiet Country Cape

RoyRating, 5 stars10 months ago
The house was perfect for us. Very clean and organized. Great host always responded in a timely manner. Was only about a 30 to 40 minute drive to Acadia National Park & Bar harbor, depending on traffic it could take longer. If we ever make it back to Maine I would definitely stay at the Higgins Retreat again. Thanks again Richard & Tina.
Guest favorite
The backyard features a fenced-in in-ground pool, surrounded by a concrete patio. Colorful floatables and pool toys are scattered throughout the clear water. Several lounge chairs are positioned poolside, providing space for relaxation in a tranquil outdoor setting.
Home in Bangor
5 out of 5 average rating, 28 reviews

New Boho Cape with Pool! Fenced yard, pet friendly

CindyRating, 5 stars1 month ago
Thank you Christina! Great weekend stay for UMaine graduation. Great location from campus and stores for the things we forgot (haha).
Superhost
A swimming pool is surrounded by paved decking, with several lounge chairs positioned throughout. A green umbrella offers shade near the poolside, and lush landscaping with trees and flowering plants is visible in the background, complemented by a clear blue sky.
Home in Lincolnville
4.85 out of 5 average rating, 13 reviews

Coastal Retreat with Pool and Cheerful Vibes

AnneRating, 5 stars8 months ago
We felt like at home. The house is located in a private property with swimming pool and tennis courts. It’s very clean and very peaceful. Just a clarification about the description : there’s no bathroom in the basement. Then if you come with elderly people or very young kids, it could be annoying. If you like cooking, the kitchen is very well equipped. We´ll keep a very good memory of our stay in Ducktrap Retreat during the colorful foliage season.
Superhost
A calm tidal pool is bordered by smooth stones and rocky edges, reflecting soft hues of pink and orange from the sunset. The tranquil water contrasts with the lush green trees in the background, creating a serene and natural setting by the ocean.
Home in Stonington
4.95 out of 5 average rating, 20 reviews

The Boathouse at Spruce Harbor

Janette Is pronounced as YanetteRating, 5 stars9 months ago
My return visit to the Boathouse was even lovelier than I hoped it would be. The location can't be matched by anything else I've seen. I enjoyed a September visit with my dog and was lucky to have pristine weather. I lived a very simple and healthy outdoors life and came home the better for it. The Boathouse is true to its description: it is simple and rustic and uncomplicated but well-equipped, and is perfect for one-and-dog, or for two people. A little coming-and-going from the neighboring houses meant that I didn't feel isolated. Margaret is truly an exceptional and friendly host who communicates promptly and clearly. I almost hesitate to share "my" Boathouse location with too many of my back-home friends because it feels so intimate and special. I already want to be back there. I offer my deep thanks to Margaret and to the place that I could - briefly - call home.
Guest favorite
An inviting outdoor space features a heated in-ground pool surrounded by neatly landscaped greenery. Lush hedges and flowering plants provide a colorful touch, while the patio area offers seating options. The well-maintained lawn completes the serene atmosphere, ideal for relaxation and leisure.
Home in Bar Harbor
4.9 out of 5 average rating, 10 reviews

Bar Harbor / In-Town 6BDRM with heated pool

ChristineRating, 5 stars7 months ago
If you’re looking to stay in Bar Harbor, this is the place! We felt very at home during our 1 week stay and walking to and from downtown Bar Harbor was easy and accessible. The house is also a 8 minute walk to the nearest grocery store so cooking your own home made meal was simple. We would definitely recommend this place to our friends and family and would stay here again!
Guest favorite
A kitchen area features wooden cabinetry and a dark countertops, complemented by wall art and decorative items. The open layout offers a view into the adjacent living room, where seating arrangements invite relaxation. Warm colors are used on the walls, enhancing the inviting atmosphere.
Home in Trenton
4.97 out of 5 average rating, 29 reviews

Acadia get away.! With pool and hot tub

JanelleRating, 5 stars8 months ago
I recently stayed with my family at this incredible Airbnb that exceeded all my expectations. This property offered a hot tub, a pool table, and a level of privacy and tranquility that made for a truly relaxing getaway. One of the highlights of our stay was being able to watch the northern lights from the hot tub – it was absolutely magical. We spent a week in Acadia, and the location was perfect, just 15-20 minutes from Bar Harbor or the nearest town. The hosts were very responsive, and the place was fantastic for families, being both kid and pet friendly. It was a week filled with unforgettable moments, and I can't recommend this place enough!
Superhost
An in-ground pool is surrounded by a concrete deck, featuring a roofed area with three bar stools. Lush greenery lines the perimeter, ensuring a private and peaceful environment. The clear blue water is inviting, ideal for summer relaxation and recreation.
Home in Tremont
4.7 out of 5 average rating, 47 reviews

Large MDI house w/pool perfect for groups+families

MauraRating, 5 stars8 months ago
We had a great stay at this house! Plenty of beds for everyone. Convenient to get to Acadia and bar harbor with a short drive!

Weekly house rentals

Top guest favorite
A fire pit area is surrounded by six metal chairs, positioned on a gravel surface under tall trees. A serene water view is visible in the background, with the sun setting over the horizon, casting soft light across the scene.
Home in Gouldsboro
5 out of 5 average rating, 27 reviews

Stunning Beachfront Chalet w/ Gameroom & Firepit

ShaunnaRating, 5 stars1 month ago
This was the perfect home to choose for our first vacation as a family of 4. Our boys loved the slide upstairs and going to explore the rocks. Even in overcast weather, the bay views were amazing from the deck and dining nook. We saw lobsterman on their boats & watched the loons. We enjoyed the game room as well! The home was clean, had everything we need, and felt like home. The hosts were very cordial and responsive. We took a trip into Bar Harbor and drove the park loop trail and also explored the Schoodic peninsula. Don’t sleep on the local Downeast Mexican takeout joint- it was amazing! We will definitely be returning with family and friends!
Top guest favorite
A vibrant sunset is captured over a serene body of water, surrounded by silhouettes of evergreen trees. The sky transitions from deep orange to soft purple hues, creating a peaceful natural scene that highlights the beauty of the Maine landscape.
Home in Gouldsboro
5 out of 5 average rating, 10 reviews

Duplex w/ocean views, no dog fees, serene location

RebeccaRating, 5 stars2 weeks ago
We absolutely loved our stay! They had everything we needed in the kitchen to make dinners for 6 people and plenty of space for us to all sit together and eat. We really enjoyed the fire pit and the beautiful views. The beds were very comfortable and everything was very clean and nice. We hope to come back soon!
Top guest favorite
A spacious deck features two blue Adirondack chairs and a small side table, overlooking a serene view of the water and surrounding trees. The deck is positioned to offer an unobstructed look at the tranquil bay.
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 spacious house is situated amidst green lawns under a clear blue sky, surrounded by trees. A gravel driveway leads to the property, which is highlighted by a covered porch at the front and a neighboring structure visible in the background.
Home in Gouldsboro
4.86 out of 5 average rating, 7 reviews

New! Spacious Private Home

Bob And AnneRating, 5 stars9 months ago
My husband and I rented this house so our nephew and his young son could visit with us. The house was very clean and we had everything we needed. Danielle was always responsive to questions and we were close to beautiful outdoor spaces.
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.
Superhost
A spacious living area displays a large sectional sofa with decorative cushions, centered around a round wooden coffee table. Natural light enters through the skylight and windows, illuminating the wood paneling and high ceiling. The open layout connects to the dining area and kitchen in the background.
Home in Mount Desert
5 out of 5 average rating, 3 reviews

4 BR Wooded Getaway on Long Pond! [Woodsy Pines]

KimRating, 5 stars2 weeks ago
We had a lovely stay and felt right at home. The house worked great for 9 of us and we could have had a few more. We loved the large dining table on the screened porch. The open floor plan meant that we could hang out together while some folks were cooking, others were reading on the couch and others were working on the puzzle at the kitchen table. Very comfortable!
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.
Guest favorite
A charming coastal home is viewed from the front yard, featuring blue shingles and a neat picket fence. An outdoor seating area with a stone pathway invites relaxation, while grassy areas frame the property. The afternoon sun enhances the inviting atmosphere.
Home in Gouldsboro
5 out of 5 average rating, 7 reviews

Lighthouse & Harbor View, an Ultimate ME Vacation

CharlesRating, 5 stars8 months ago
What a beautiful house in a lovely setting! The historic details with modern kitchen and baths made this a perfect home base for exploring this lesser known part of the Maine coast. Proximity to Schoodic Peninsula (part of Acadia National Park) allowed for great hiking and incredible views. Some great restaurants are close by. We particularly liked the Tree House in Winter Harbor and the “Pickled Wrinkle” in Birch Harbor. The house is clean, comfortable and well equipped. We especially loved the backyard fire pit. Having dogs in tow, we REALLY appreciated the fenced yard. Views of the sunset from the front yard were just stunning. We will definitely be back!

Private house rentals

Guest favorite
An aerial view of a coastal property surrounded by lush greenery and trees along the water's edge. The home features a brown roof and is set against a backdrop of a blue-gray sea and a sky with scattered clouds. The rocky shore is visible, emphasizing the natural landscape.
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.
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 :)
Superhost
A cozy living area is presented with a light-colored couch and decorative pillows. Large windows offer views of a tranquil tidal water landscape, revealing a dock and lush greenery beyond. Natural light brightens the space, enhancing the inviting atmosphere.
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 favorite
The kitchen features modern cabinetry in a deep blue hue, paired with light wood countertops. Open shelving displays dishware and plants, while stainless steel appliances line one side. Natural light enters through a window above the sink, complemented by decorative light fixtures.
Home in Franklin
4.97 out of 5 average rating, 61 reviews

Sunrise Over Schoodic Mountain

SageRating, 5 stars1 day ago
We felt so at home at Travis’ place. We had a late check in, and I will say he was right when he said it’s tricky to find in the dark! Once we got there and looked around it got easier. Everything was so clean and cozy. We loved having the two bedrooms right next to each other. It made it easy for our young daughter to get us if she needed us at night. The view alone made us feel so at peace that not much could top it. We also appreciated the access to tvs, but not making them stick out in the home. Everywhere we went was between a 30-45 minute drive which we did not mind at all. We actually quite enjoyed it so we weren’t right by all the craziness of some of the tourist towns. I can’t say anything but amazing things about this house. If you’re looking to book and this house ends up on your list.. just book it!! You won’t regret it.
Guest favorite
A side view of the house highlights weathered shingles and large windows, complemented by vibrant pink flowers in the foreground. The Atlantic Ocean and distant islands are visible in the background against a clear blue sky.
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!
Top guest favorite
A spacious deck overlooks tranquil waters, featuring four brightly colored Adirondack chairs and a kayak rack holding two complimentary kayaks. The backdrop consists of a serene coastline and gently rolling hills beneath a partly cloudy sky.
Home in Trenton
5 out of 5 average rating, 34 reviews

Relaxing Acadia Beachfront Cottage.

BethRating, 5 stars2 weeks ago
We loved our three nights at Seabank. The house was comfortable and immaculate, the kitchen well equipped, and the location—overlooking tidal Goose Bay with views toward Mount Desert Island—could not have been more tranquil (plus an easy 20-minute drive to Acadia/Bar Harbor). Robard was a terrific host, quick to answer our questions, and even lending a hand to ensure that we were able to check in early. We lucked into gorgeous weather and spent lots of time outdoors, reading on the deck, kayaking in the bay at high tide, and relaxing around the fire pit.
Guest favorite
A quaint cottage exterior is framed by lush greenery and blooming flowers. A wooden window features frosted glass, softly illuminated from within. Surrounding plants include vibrant pink peonies, contributing to the inviting garden scene.
Home in Surry
4.97 out of 5 average rating, 67 reviews

The Surry House | Cozy Cottage by Acadia, Fire Pit

LucindaRating, 5 stars2 weeks ago
Really cool little house in a great location for exploring Acadia NP/Blue Hill/Deer Isle region. The house is small, but it’s set up to really use the space wisely. It’s really nicely decorated also. Had everything we needed. Union River Bay is just down the road where you can watch the seals frolicking. Had a great stay! Ice cream store is only a 2 minute walk. Bonus!!
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.

Quick stats about house rentals in Winter Harbor

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ551 before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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  4. Hancock County
  5. Winter Harbor
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