
Cottage holiday 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
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!

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!

Megunticook Retreat
The perfect place to stay for a peaceful vacation - the home is extremely well appointed and had everything we could possibly need and more. The lake is even more beautiful than the photos and we enjoyed the kayaks and hot tub each day we were there. We would highly recommend.
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 #7 at Lewis Cottages
This was a lovely stay with easy and convenient access to all of the main island's adventures. We had an unpredictable schedule and Jay and Lisa were very helpful and facilitated self checkin and checkout so we could hike and not worry about arriving/leaving at a precise time.

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!

Harborview~Seaglass Beach~Firepit~5 min to Acadia
Wonderful place in a great location! Kristen was super responsive and has even able to accommodate us day-of (even a few hours of!). We have been coming to the island for 25 years and actually have a property not too far away on the island but needed a place just for one night - Kristen’s place was a wonderful change, and knowing the island very well, I can say with confidence that it’s a great place to stay!
Private cottage rentals

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

Right on the ocean! (2)
We were immediately charmed by this pristine, cozy cottage by the ocean. The view is incredible and the atmosphere relaxed and inviting. Ashley and her hospitality crew are so friendly and helpful. Felt like we had known them for a while! Very difficult to leave this beautiful place.and hope to return someday.

Exquisitely Modern Maine Cottage @Diagonair
We were very comfortable in Ann’s home. It is quite beautifully designed and furnished. Very quiet in the woods. The home was very functional too; it had everything we needed and was easy to settle in. It seems that Ann has given a lot of thought to what her guests will need - way more than what one would expect.

Owl Glass Cottage
Wow! Annie’s cottage is nothing short of amazing. It was absolutely beautiful and the perfect intimate stay my boyfriend and I were looking for. The surrounding area is beautiful as well! The space was perfect for the two of us and so so peaceful!

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!

Virginia's Sunset at Sunset Cottages
What a beautiful location! We had such an amazing time on our honeymoon staying at Sunset Cottages and visiting Acadia all week long!! It was such a quiet peaceful location that felt like the perfect home away from home! We would love to return in the future someday for an anniversary! : )

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!
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
- Kebo Valley Golf Club
- Spragues Beach
- Bear Island Beach
- Sand Beach
- Gilley Beach
- Narrow Place Beach
- Pebble Beach
- Pobblestone Cove
- Lighthouse Beach
- Hunters Beach
- Indian Camp Beach
- Orchard Beach
- Great Beach
- Sandy Point Beach
- Wadsworth Cove Beach
- Redman Beach
- North Point Beach
- Driftwood Beach
- Three Island Beach
- Billys Shore
- Islesboro Town Beach
- Hero Beach