
Cottage vacation rentals in Winter Harbor
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Top-rated cottage rentals in Winter Harbor
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Popular amenities for Winter Harbor cottage rentals
Cottage rentals with a hot tub

Lakeview Cottage
This house has a beautiful view of the lake!! The complementary water activity’s are worth booking!! We enjoyed our stay and will come back!! Make sure to walk out on the dock at night and look at the stars!!

Waterfront Great Pond Cottage w/ Hot Tub & Deck!
Our stay at the Great Pond Airbnb was incredible! The house was beautiful, cozy, and fully stocked with all the amenities we needed. We especially loved the paddle boat—it was magical to take it out on the lake early in the morning and watch the sunrise. Truly a dream! Finding the place initially was a bit tricky (we missed some details in the instructions), and cell service in the area is spotty, so definitely screenshot directions beforehand. Once settled, though, it was perfect. Being just over an hour from Acadia National Park was a huge bonus! We had a blast hiking, especially on Precipice Trail (challenging but amazing!) and Beehive Trail for a slightly easier, but still fun option. This spot offered the perfect mix of relaxation and adventure. Highly recommend it if you're looking for a peaceful, nature-filled getaway!

Penobscot Bayview Fireplace Hot tub
It’s a lovely cabin, the hot tub is a plus. It’s also fairly private since it’s last cabin of the property.

Canoe House Bungalow and Spa Retreat ,Searsport
We had a great two nights here and enjoyed the hot soak and the sauna. It was near many amenities and also felt very removed. Matt’s was attentive without being intrusive, making sure our stay was perfect and the escape we hoped it would be.

Lawn Cottage - Newly Renovated 2024
Adorable cottage, newly renovated. Perfect for two with an open space loft for one more. Kitchen is well stocked right down to the coffee. A good location if visiting Fort Knox, Mt. Barrie and not too far from Bar Harbor if that is on your list. Great stay, highly recommend. Beautiful view and private.

Nashport on the Penobscot
great stay for a relaxing weekend trip. perfect house for chilling but still drivable to Acadia. well stocked on the essentials, linens, and stunning views! host very responsive as well.

Open Hearth Inn Cottage 12 - 10 min to Acadia!
A great stay! It is close to the Acadia NP. The place is quiet and clean.

Megunticook Retreat
We’ve stayed in a lot of Airbnbs across the country and I’m not exaggerating when I say that Lydia’s place was one of the cleanest and most well-maintained homes that we’ve been in. The property and scenery are breathtaking. The numbers of birds and chipmunks that entertained us while we sat on the back deck was surprising. We ate all of our meals with the exception of lunches at the cabin and had everything we needed to prep and cook our food. This trip was all about relaxing and Lydia’s home was everything we needed.
Pet-friendly cottage rentals

Chic Farmhouse Cottage, WiFi, Private Beach, A/C
Absolutely loved our stay here! If you're someone who enjoys being close to nature and traveling with your dog, this place is perfect. The surroundings are peaceful and green. Fabiola was super friendly and made everything easy from check-in to check-out. The house rules were clear and straightforward, which made the whole experience stress-free. We felt really welcomed and comfortable the entire time. All in all, a great stay—we’d definitely come back!

Everett Cottage at Indian Point (Bar Harbor)
What a cool house! Very unassuming from the pictures. It's like a time capsule -- shag carpet, retro wallpaper, vintage fixtures and paneling. Although old, everything was clean upon arrival. I love old things so I enjoyed the aesthetic, although for someone with heavy allergies or sensitivities, the age and moisture may be something to consider. That being said, I have chronic allergies and sinusitis and I would 100% stay here again. The property itself is the focal point and the draw. It's set on a point of the cove where you can hear and see the seals in the distance, and you feel like you're on an island. While we were there, the sun came up at 4:30 every morning and we were out on the back deck at 4:45 with coffee in hand. So peaceful and serene! Use of their kayaks and life vests was an added bonus -- note to self, the islands in the distance are further than they look!! :) The kitchen was well equipped for cooking, and we enjoyed the use of the back grill. Lovely home!

Modern cottage with hummingbirds
We liked the privacy and seclusion of the house, as well as, having good wifi and space for our dog. The windows around the house let in so much light and we could see wild turkeys in the field one night. The house is close enough to what Acadia, Ellsworth, and Bar Harbor has to offer, but is away from the congestion. Having a washer/ dryer is a plus. We had a great stay of 5 days.

Cozy cottage in the woods
Cute little cabin in the woods!! Super clean, check in was very easy. Nichole was very easy to communicate with. The cabin was perfect for a quick weekend. We would definitely stay again!

Camp on private Beach / Bears Den / Graham Lake
I had a wonderful stay here! The inside is clean and cozy! Plus we enjoyed being able to cook over the fire and hang out by the lake. The location is private and peaceful. 35 minutes to the entrance of Acadia but depending on what part of the park you are headed to it can be up to an hour drive. I would stay again!

Lakefront Stargazing Haven w/Loons, 45 Min Acadia
We had an amazing stay at Jason’s place despite a (mostly) rainy Memorial Day weekend! We still found plenty to do including inside the Airbnb, outside at the pond, and locally at all of the great restaurants/breweries/nature around. We also made it out to Acadia two of our days. I will say, the trip took longer than advertised (about an hour to get to the edge of the park), but was a pleasant enough ride. We also had our two dogs staying with us and we all felt right at home! Jason was a very responsive and helpful host as well - you can’t go wrong with this peaceful retreat on the pond!

Cottage #8 at Lewis Cottages
Lovely space and close to Acadia! Had everything we needed!

Acadia Access Cottage-Bar Harbor
Philip's home is one of our favorite Airbnbs. The location is private yet close to the carriage trails and bar harbor. The windows overlooking the trees make us feel like we're in a tree house. Everything works and the hosts are quick to respond to any issues. We highly recommend it!
Private cottage rentals

Oceanfront Island: Hiker & Honeymooner’s Paradise
Jane and her cottage were spectacular. We were looking for a place to unwind and decompress, and this was all that plus the bonuses of a luxuriously appointed, thoughtfully decorated and absolutely spotless home, with an unparalleled view of the ocean in its ever-changing moods, shimmering sunsets and moonrises, cavorting seagulls and flocks of geese, and a soundtrack of waves, songbirds and gull calls. We felt welcomed like houseguests at a good friend's home who had just stepped out for a little bit. We forgot to look for the fabled map drawer (mentioned by another reviewer) but were intrigued by the many books on the shelves by Maine authors, and short stories that we read aloud to each other. One of us walked the 4.5 mile loop trail, rugged but well worth the effort, if one is up to it, for the wild coast and ancient forests. We both sat on the chairs at ocean's edge to drink it all in. This was the very best B&B we've ever stayed at. Kudos to Jane for making her home available!

'Tugwassa' On Down East Jones Pond- poet's cottage
My mother and I loved our stay at Tugwassa. When we weren’t exploring the nearby area, we spent our time looking out at the pond, enjoying the fire, and reading Mrs. Osborne’s poems! The cottage is beautifully decorated with a well-equipped kitchen. I loved taking the time to appreciate all the artwork and ornaments. Anne is very welcoming and hospitable - she has many great local recommendations and is nearby if you need any help. I’m looking forward to coming back again!

MaineStay Cottage #1 Bangor/Hampden full kitchen
Great little cabin, could immediately tell that the hosts cared about doing things right and thought about the little details. Would definitely come again.

Sleep next to the ocean in Gouldsboro!
This is an absolute gem of a place on the quiet side of Acadia on the Schoodic Peninsula. Fantastic view of the harbor where you can watch the fishing boats coming and go. Extremely well appointed cabin with all of the essentials. Nice quilts, fluffy towels and lots of nice large mugs. Walk next door to a fabulous seafood restaurant. Couldn't ask for a better location.

Cottage near Lighthouse, Trails, Ocean & Seafood
great location walkable to the busy bass harbor lighthouse, no need to find parking! we spent 4nights as a family of 4 it was wonderful quiet and cozy location with easy access to trails and all that acadia has to offer! we would absolutely come back

Oceans edge Unbeatable views! (1)
Absolutely loved my stay here! If you’re looking for somewhere very rural, quiet and secluded, this is a perfect place. It’s fit for one or two people, it was so incredibly cute and whimsical, definitely the best place I’ve ever stayed!

Ledgewood Grove Cottage in Bar Harbor
Our stay was very nice, comfortable and the cottage well supplied. The cottage was very cozy with plenty of room. We liked how quiet the place is and could sit outside and enjoy the nice day. Close to town and restaurants and all that Acadia has to offer. We hope to be back again. Thanks Robin & Dirk.

Little Gem- Waterfront Cottage Near Schoodic
We LOVED our stay at Little Gem! It was absolutely perfect for what we needed. We loved being able to access Acadia from there. There were also so many great opportunities to explore the local area as well. It was amazing to come back and relax at the end of the day with a beautiful view! Nicole and Russ have thought of all of the details. They provided so many great recommendations for the area. They were always quick to respond to our questions. We could not have asked for a better stay.
Quick stats about cottage rentals in Winter Harbor
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ661 before taxes and fees
Total number of reviews
350 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Schoodic Peninsula, Schoodic Point, and Schoodic Woods Campground
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- Acadia National Park
- Northeast Harbour Golf Club
- Kebo Valley Golf Club
- Sand Beach
- Three Island Beach
- Spragues Beach
- Hero Beach
- Narrow Place Beach
- Lighthouse Beach
- Bear Island Beach
- Gilley Beach
- Pebble Beach
- Wadsworth Cove Beach
- Sandy Point Beach
- Pobblestone Cove
- Hunters Beach
- Billys Shore
- North Point Beach
- Driftwood Beach
- Islesboro Town Beach
- Great Beach