
Cottage holiday rentals in Winter Harbor
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Top-rated cottage rentals in Winter Harbor
Guests agree: These cottages are highly rated for location, cleanliness and more.
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Popular amenities for Winter Harbor cottage rentals
Cottage rentals with a hot tub

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.

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!

10 1BR Acadia Cottage w/AC Open Hearth Inn
Great price, perfect location for Acadia visit and cute little place. Will return for sure!

Penobscot Bayview Fireplace Hot tub
This place is a gem! The pictures don't do it justice. Perfect getaway for a couple, the cedar hot tub is so nice and has views of the ocean! Great hiking nearby and fun food/drinks in downtown Camden (the Vintage Room has a great happy hour).

Canoe House Bungalow and Spa Retreat ,Searsport
We enjoyed our weekend away at Mayya’s guest house! It was the perfect size for the two of us and we felt there were more than enough amenities to ensure our stay was cozy and peaceful! The add on of the hot tub was much needed and appreciated as well as it was getting chillier at night and it was the perfect addition! I would have liked to take advantage of the walking trail but the weather was rainy so we didn’t get to. We would definitely stay here again for a couple days and thank you Mayya for being a great host!

Lawn Cottage - Newly Renovated 2024
What a cute cottage with absolutely everything one would need Killer view

Nashport on the Penobscot
This was our second time staying here, my family and I love the tranquility of this little piece of heaven. Christopher’s home was beautiful, clean and well maintained.

14 1Br Cottage in Bar Harbor Open Hearth Inn
Wonderful location! Right outside Bar Harbor and a quick drive to Acadia. Had a great stay. Will for sure be back!
Pet-friendly cottage rentals

Stonington Harbor Cottage - Vacation / Remote Work
Fantastic spot. The cabin is so well equipped and squeaky clean. Maggie has thought of everything! Walkable to town in minutes and private. There are even glimpses of the sparkling ocean. 5 stars!

Chic Farmhouse Cottage, WiFi, Private Beach, A/C
This cottage is delightfully cozy in the winter and very charmingly decorated. It’s not just run of the mill decor. The lighting setup is especially great and was put together very thoughtfully. I really enjoyed being IN the spaces that have been created in the cottage - there are several different seating areas for reading a book or sharing a meal or hanging out. The location of the cottage is spectacular with beautiful views from the windows as well as the private garden, private porch overlooking the bay, and more. Fabiola leaves many helpful instructions (often amusing!) and also gives lots of recommendations about the area. In addition to that she is super welcoming, always available, and clearly wants her guests to enjoy themselves. She also lets the guests have privacy. I’m sure the cottage and garden are even better in summer simply because one can spend more time outdoors, but winter has its own beauty in Maine and the cottage is a wonderful place to experience it from.

Cottage/w beach, hiking, boat lounge, shown on HBO
It's our second time staying here, and we again had a wonderful time catching up on literature, soaking up some sun on the porch, and breathing in the salty air in this beautifully decorated home. Many fantastic nature adventures are just a short drive away. Julie and Rich are responsive and gracious hosts.

Peaceful Branch Lake Cabin minutes to Acadia
It was just great, wish we stay longer, and we will definitely be coming back, we hope to book for longer and I think we would like to come back in the summer months. Acadia was beautiful, we were able to use the canoe and go into the lake, set up a fire, and make s'more.

Cozy Cottage on Frenchman Bay
We stayed at Alicia’s place, as we were traveling through, so we didn’t get to take full advantage of the lake. It was well appointed and made great use of the space. There was only 2 of us but a family of 4 would have no issues. It was extremely clean and cozy. We would stay again if in the area. Thanks Alicia

Lily Pond Studio Cabin #4
We loved our experience at our cozy, stand alone cabin. The room is spacious and has everything you need. We would stay again for sure!

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!

Spring 2025 Waterfront Getaway! Hi-Speed Wi-Fi
We loved our stay here! The views of the water are amazing. It was the perfect place for us to relax and recharge from our travels. We spent a rainy day at the house and took a walk down to the water exploring the low tide and finding little treasures from the sea. What a cool experience right outside the home! We went to Acadia and Bar Harbor during our stay here, which was about an hour drive. Beautiful drive! Great place to stay that made us feel right at home. Thank you for your hospitality!!! We would stay here again in a heartbeat! ❤️
Private cottage rentals

The Green Cottage@ Twin Hills Cottages
Jon’s place is beautiful and conveniently located. Would come back again!

Lakefront Cottage on Tracy Pond, New Hampshire
The Twisted Calico is our favourite in our adventure! Soo cozy, beautifully decorated, equipped with everything, hosts were soo gracious & welcoming. We were privileged to meet them. :0) Anna affirmed our dinner choice - it was PERFECT!! We would definitely return- can’t wait to see their new reno’s to the Twisted Calico. We ABSOLUTELY LOVED our stay 💯 & will tell all our friends & family. Thank you sooo very much 🥰

The Cottage
We had a wonderful time at Darthia Farm! We enjoyed sunrise down by the water and loved the short, but beautiful trail that led us right down to the water. We thoroughly enjoyed visits from the farm dogs and cat! The simple amenities really helped us to slow down and be intentional, even the way we washed the dishes. It was all very peaceful and what we needed. Even in the brisk weather of October, we enjoyed the outdoor shower! We cooked a delicious dinner one evening with yummy pesto and other goodies from the farm store (goat milk gelato was 🔥). Shepsi recommended some local hikes and on our last day ,we ventured over to Petit Manan wildlife refuge and hiked the Hollingsworth trail... absolutely stunning, and easy trail. Our stay here away from the busy tourist places of Maine was perfect!

Acadia area cove with canoes! Sun-Sun weekly!
Believe the reviews! If you get a chance to rent here in the fall (or any time) you won’t regret it. I wish I could’ve stayed and read all of the cool books. Perfect space to gather but also have your own little corner if needed. Plus - the views are unlike any I’ve experienced at an AirBNB. Truly beautiful at any time of day. Plus our dog loved running around in the fenced in yard. We can’t wait to go back!

Periwinkle Cottage - in Brooklin, Main
This cottage and the beach on which it is situated are breathtakingly beautiful. we immensely enjoyed the tranquility, the exquisite and simple aesthetic of the cottage, the privacy and length of the beach for walking at low tide, the coastal birds, and the time we had to relax. If I were to return I would do a few things differently: I would bring water shoes for walking on the beach and in the low tide, a mosquito head net, and a sun hat. I would also ask the owner to let me know when they expect the mowers to come so that I would be sure not to be doing some thing like meditating when they arrive. They arrived on huge lawnmowers and although they finished their business in quick order it was still a bit shocking to the nervous system. Overall, this was one of the best experiences I have had with Airbnb.

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!

Cottage nr Acadia NP, King bed, AC, beach sunsets
This cabin is exactly what we were looking for. It’s a decent sized space with a nicely equipped kitchen, full bath and a king-sized bed (Along with a separate bedroom that we never used). The couch/futon is also quite comfy. The cabin has everything you need and possibly a little more. The location is fantastic as you’re just 10 minutes to downtown Ellsworth, which is full of nice shops and plenty of places to eat. It’s a little less than an hour to Bar Harbor, which is also very convenient. Don’t ignore the nearby rocky beach that is a short walk away and beautiful, especially in the evening. We had quite a haul of seaglass too! This is a great place with great hosts that were responsive and helpful. We can’t wait to go back!

Quaint Oceanfront Island Cottage, off Bar Harbor
Barnacle Hall was the peaceful backdrop for a birthday getaway. We were gifted with rain, but the cottage, Kyle, and the locals of Swan Island kept our spirits and our body temperature up! Kyle supplied space heaters, and provided through instructions for making a fire as well as instructions for everything you need to know for your stay. His recommendations for exploring the Island did not disappoint. Highly recommend TIMS market, Fine Sand Beach, the Lighthouse, and waking up early in the morning to listen to the birds, and experience the tranquil view from the backyard of the cottage.
Quick stats about cottage rentals in Winter Harbor
Total rentals
10 properties
Nightly prices starting at
$281 AUD before taxes and fees
Total number of reviews
350 reviews
Wi-Fi availability
10 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
Local attractions
Schoodic Point, The Pickled Wrinkle and Schoodic Woods Campground
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- Acadia National Park
- Northeast Harbour Golf Club
- Narrow Place Beach
- Spragues Beach
- Sand Beach
- Bear Island Beach
- Kebo Valley Golf Club
- Gilley Beach
- Pebble Beach
- Lighthouse Beach
- Pobblestone Cove
- Hero Beach
- Hunters Beach
- Orchard Beach
- Indian Camp Beach
- Islesboro Town Beach
- Sandy Point Beach
- Wadsworth Cove Beach
- Redman Beach
- North Point Beach
- Driftwood Beach
- Three Island Beach
- Billys Shore
- Great Beach