
Cottage holiday rentals in Winter Harbor
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Top-rated cottage rentals in Winter Harbor
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Popular amenities for cottage rentals in Winter Harbor
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
We had a very relaxing vacation. Verona Island is convenient for day trips to a number of attractions like Acadia, Camden and even Monhegan Island. Even when the weather was bad there was plenty of table space for puzzling, Bananagrams and Scrabble. The house was comfortable with views of the Penobscot River.

Open Hearth Inn Cottage 12 - 10 min to Acadia!
Perfect place to stay outside of Mt. Desert island. Right on the main rd so could be a little noisy but worth it for convenience. Place is very clean, cozy & spacious for two of us & our dog! Would book again!

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

Lake Front-Spa Tub-Fire Pit-Full Kitchen-Canoe
The location was perfect for our trip. The house it self was extremely clean and lots of space for us to hang out and also have our space. Close to Acadia which we visited Saturday and the house was a great distance to enjoy the day without staying in town! The amenities were in great condition and everything in the listing was there. I would definitely stay again.

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!

Lakefront Cottage on Tracy Pond, New Hampshire
This was great cozy, cottage. We we were pleasantly surprised! The inside was very nicely decorated and was definitely enough space for my husband and I, and our two dogs. It was so nice to relax enjoy a sunset and make a fire in the fire pit after a long day. We were greeted by the welcome committee (black cat) numerous times. The cottage had everything we needed. My dog really enjoyed swimming in the lake. Thanks so much and we would definitely consider staying here again

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!

Lakefront Stargazing Haven w/Loons, 45 Min Acadia
Tucked in the woods of Orrington, Maine, this lakeside retreat offers a rare kind of stillness. Facing south on the water’s edge, it provides serene views of both sunrise and sunset that frame each day in quiet beauty. Wildlife is abundant, loons echo across the lake and deer move gently through the trees, yet the home is only a short drive from Bangor’s restaurants, trails, and conveniences. We initially booked for three nights but quickly extended to four. This place invites lingering. It’s easy to settle into the rhythm of the land, the lake, and the quiet. Inside, the home is curated with care including a lovely vinyl collection; late night jazz and morning classical set the perfect tone for slow coffee and reflection. The host was responsive and thoughtful throughout, making everything seamless. We will absolutely return and recommend this home to anyone seeking not just a place to stay, but a space to truly be.

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!

Summer 2025 Waterfront Getaway! Hi-Speed Wi-Fi
Stephen's place is a gorgeous getaway for a fam. it's literally ON the ocean - with multiple jaw dropping views. Best part was the view from Dining room! clear and crisp communication and great stay. would recommend 10/10.

Acadia Access Cottage-Bar Harbor
We loved our stay. Super convenient location to all Acadia NP has to offer. About 10 minutes to get to Bar Harbor. We especially loved the privacy and serenity of the property. If you want to get away to a private place, this is perfect. We also loved having the EV charging. I don't know if we could have visited Acadia without it. Philip was a great host and gave awesome recommendations.
Private cottage rentals

Cobblestone Beach Cottage
⭐️⭐️⭐️⭐️⭐️ This place was pure serenity. My mother, my children, and I had such a memorable stay surrounded by breathtaking scenery and the peaceful sounds of nature. One of the most special parts was being able to watch marine life right from the shore — something my kids were absolutely fascinated by. It was our first time in Maine, and it was exactly how we imagined it: stunning coastlines, fresh ocean air, and a quiet charm that made us feel instantly at ease. The host was incredibly kind and gave us helpful recommendations for places to visit, which really made our trip even better. I can’t say enough wonderful things about this stay. It was relaxing, beautiful, and gave us memories we’ll cherish forever. Highly recommend to anyone looking for a truly special getaway.

Camp Tranquility @ Rock Cove
Excellent place to relax . Host is friendly and responsive. Plenty of activities and amenities.

'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!

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!

Hoover's Cottage Retreat
The cottage was an awesome stay. Beautiful views of the water from the front porch/fire pit area, super clean and useable space. Luis is a helpful and responsive host, with clear instructions to find and access the cottage. Thanks much!

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.

Cozy Cottage on Blue Hill Farm
This is an absolute charmer of a cabin on a quaint, quiet farm- including a view of a couple of very happy pigs in their large pen. Acadia, Stonington, and more great destinations are easily drivable but I can also attest that the WiFi worked great, as I had to squeeze some work in. I would love to return and would recommend staying here to anyone!

Secluded Acadia waterfront cottage on Taunton Bay!
The cottage was so cozy and peaceful. We loved relaxing and enjoying the view. We arrived in the dark and Kelly was very responsive when we had troubles because of that. Would definitely stay again!
Quick stats about cottage rentals in Winter Harbor
Total rentals
10 properties
Nightly prices starting at
$232 SGD 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
- Three Island Beach
- Spragues Beach
- Hero Beach
- Sand Beach
- Gilley Beach
- Pebble Beach
- Narrow Place Beach
- Lighthouse Beach
- Bear Island Beach
- North Point Beach
- Billys Shore
- Driftwood Beach
- Wadsworth Cove Beach
- Sandy Point Beach
- Islesboro Town Beach
- Hunters Beach
- Pobblestone Cove
- Great Beach