
Winter Harbor vacation rentals
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Top-rated vacation rentals in Winter Harbor
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Winter Harbor cottage rentals

Belfast Cottage
Dan's cottage provided everything that the three of us needed for our weekend stay. We enjoyed a walk on the nearby beach, and were able to explore the city of Belfast, which is charming and artsy. If we'd had more time we would have checked out more restaurants, galleries, and shops. There was a great food co-op in town where we picked up meals and snacks for cozy dinners and board games at the cottage. The beds were comfy, the place was clean, and it was about a one hour drive to Acadia National Park where we spent most of our time while we were in Maine.

MaineStay Cottage #1 Bangor/Hampden full kitchen
We have stayed at this location before and loved it. The second time was just as amazing. Such a cute relaxing cottage with everything you need. The home was a great place to unwind and relax. The special touches and cleanliness is top notch. Highly recommend this place. We will be back again for sure !!

Cottage on the lake
Kurt and Jackiee were incredibly helpful and friendly. We loved staying at their cozy little cottage that had great views of the nearby lake! Would recommend to others looking to stay in a more secluded area that is still a good distance from Acadia National Park.

Modern cottage with hummingbirds
A very cozy and well equipped cottage. Enjoyed the peace and quiet after a long day. Great place to stay for visiting Bar Harbor and Acadia National Park.

Quiet lakefront cottage on Graham Lake
This location is absolutely beautiful! The incredible views on this private lot are enough to make it worth it. The cottage has a modern touch, with a rustic outdoor feel. Perfect for a little family getaway. It truly is right on the lake, and has plenty to do in the surrounding towns for food and shopping. Deb is a very communicative host. Highly recommend booking with her and her family on their quaint farm!

Quiet Lakeside Cottage
Our family had a lovely stay at the Lupine Cottage. Such a peaceful spot. We enjoyed getting out on the water in the kayaks and sitting out in the Adirondack chairs listening to the loons and barred owls call. Nice central location for exploring Acadia and the mid coast. Thanks Kim & Stacy for the precious memories!

The Otter Cottage at Bay Meadow Cottages
Great cottage to stay in!

Castine rustic cabin coast forest Acadia Wi-Fi
Amazing and beautiful location! Super quiet at night and only a few cars driving by during the day. Cheryl was super communicative and had stocked the house with everything I could possibly need- gear for any kind of excursion, plenty of cookware, extra linens, even toothbrushes in case you forget. Perfect as a home base for exploring the area or for a quiet retreat. Also has an amazing, spacious kitchen, so great if you like to cook!
Other great vacation rentals in Winter Harbor

Rustic Home on Private Pond
Perfect location for Acadia if you are looking to be in a rural location around a hour or so drive. Blue hill avoids the hustle and bustle of bar harbor. Daniel’s place has an extended back yard to a pond and the scenery is gorgeous. No issues at the home, everything was great and Daniel reached out several times to ensure all was well. Recommend to all.

Lakeview Cottage
Really enjoyed our stay here. The views were lovely, the lake was refreshing, the beds were comfortable, lots of kitchen stuff, and the showers were hot. The house mostly has what you need. It could use a few more dish towels and bath towels. The long drive to Acadia got tiresome.

The South Bay Cottage "on the rocks"
Pine panelled cabin in the woods above the bay with clear view of the water and access to the dock via a path. Very peaceful and quiet. We saw a seal swimming; many birds and great dark sky for star watching. We went at a cool time of year and there was abundant rain so we could not make use of the screened porch which in the summer I imagine would be very relaxing. The cabin had all the needed amenities and then some. Minor issue was managed speedily by the host. It is the perfect place for kayaking but alas that was not possible because the Activity Shop was closed for the season.

Oceanview Escape near Maine Beaches
What a cozy, beautifully furnished and decorated space. A lot of thought went into making guests feel they’re staying somewhere very special. We certainly did. The second floor apartment with its spacious deck had a view of the ocean and some spectacular sunrises. This was our first visit to Maine and we wanted somewhere central on the coast, like Owl’s Head. It was a good base to explore from. And there was lots to do close by. We were especially pleased to discover the Bernard Langlais art preserve only a few miles away. Rockland is ten minutes away and has a lot of great places to eat.

Lakeside Landing
My husband and I spent our babymoon at Jennifer’s place, and waking up to the stunning lake view each day was just what I needed to unwind. I asked Jennifer if there was cooking oil available, and her mom kindly brought us a bottle of olive oil before our arrival—such a thoughtful gesture! We will definitely stay here again if we're ever in the area.

Lovely waterfront in Trenton.
The house and views are excellent, you can sit on the back deck or outside area and just gaze out at the view, see Bald Eagles fly over every day, even saw one grab a fish from the water. Very clean and well appointed with the essentials like detergents for laundry and dishwasher, garbage bags, slat, pepper and other cooking basics, foil and cling wrap, beach chairs. Overall I can say it is a very nice house, very clean. The location is 20 - 25 minutes from Bar Harbor and maybe 20 min to Acadia. We didn't mind this at all. We ate lobster at 5 different places, if you want the absolute best Lobster rolls go to the Travilin Lobster, there is one in Trenton and one in Bar Harbor, by far the best lobster roll. Oh, and probably as important as the house being very clean, the beds were very comfortable.

Acadia Beach shipwreck cottage Bar Harbor
We had a wonderful stay! The location is perfect—very close to Acadia, making it easy to explore the park. The house was extremely clean, well-maintained, and had comfortable beds with great sheets. The host was very responsive and helpful throughout our stay. The only thing to note for families with young children is that there are stairs and space heaters, which might require some extra supervision. Overall, a fantastic place to stay, and we would definitely return!

Lakefront Log Cabin on Pleasant Lake
This was our second stay with Devon and as usual it did not disappoint! It is exactly what we needed for a quiet getaway. It is very serene with sounds of the Loons echoing across the lake. Did not see a car or person in 4 days which was great. Devon was always in touch if needed and accommodating. Great kitchen with everything needed for a snack or a full meal. A very relaxing stay!
Quick stats about vacation rentals in Winter Harbor
Total rentals
100 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
3K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Frequently Asked Questions
What types of vacation rentals are available in Winter Harbor?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Winter Harbor. From over 50 house rentals to over 10 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Winter Harbor?
Yes! Work meets play with ease at over 50 vacation rentals in Winter Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Winter Harbor?
Four-legged friends are welcome in Winter Harbor. Choose from more than 30 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Winter Harbor?
Experience the best of Winter Harbor with our cottage rentals, starting at about $180 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Winter Harbor have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Harbor have self check-in?
Absolutely! We offer over 20 house rentals with self check-in in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winter Harbor have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winter Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winter Harbor?
Winter Harbor has more than 50 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Acadia National Park
- Spragues Beach
- Narrow Place Beach
- Northeast Harbour Golf Club
- Sand Beach
- Gilley Beach
- Kebo Valley Golf Club
- Sandy Point Beach
- Pebble Beach
- Wadsworth Cove Beach
- Great Beach
- Pobblestone Cove
- Hunters Beach
- Billys Shore
- Hero Beach
- North Point Beach
- Three Island Beach
- Driftwood Beach
- Orchard Beach
- Islesboro Town Beach
- Bear Island Beach
- Lighthouse Beach
- Indian Camp Beach
- Redman Beach