Vacation rentals with a kayak in Cumberland County

Stayed at Bethany's place for a long weekend at the end of the season. The location is unbeatable, the house is situated on its own little peninsula in a stunning cove; it feels very private and has amazing views of the water. There's tons of outdoor space and seating, along with several kayaks. The house itself is clean, quiet, and peaceful, although it's definitely small--probably best for one or two people, or a couple with a small child. Access is down an unpaved road but Bethany's very clear instructions made it easy to find, and she was responsive to any questions we had. Harpswell abounds with areas to hike and explore, lots of good places to eat (though you will definitely need a car) and is less than an hour from Portland and only half an hour from Freeport.

Had an amazing time, house is absolutely beautiful. The area is super quiet as well which we all appreciated. All 6 of us who stayed there this past weekend highly recommend staying here. ☺️

GREAT FIND!! Don & Nina were fantastic hosts! We LOVED the location. We were welcomed with fresh flowers in a vase on the dining table, and we enjoyed our meals together there as well. We greatly appreciate how CLEAN the entire place was. The setup of their place was just perfect for us and our parents! We love to coo k, and the kitchen is well-appointed! The beds and pillows were very comfortable giving us a good night's sleep each night. The full-sized bedroom has a mini split which adds to the warmth or cool (whichever is needed). The master bedroom with a queen bed is large and comfortable. Our parents loved the two rocking chairs, and we enjoyed the comfy couch and chair. Even though we didn't have the greatest weather during our stay, we were able to get out on a kayak and enjoy the lake. The house is nestled in a very quiet cove on the lake and, because there is no public access to the lake, the entire lake is a fantastic find! This will be an annual stay for us now!

Such a beautiful and peaceful place!! my kids didn’t want to leave! Lovely cottage feel with a beautiful view to the lake. We had such a great time taking the kayaks and paddleboard out on the water and enjoying our coffee overlooking the water from the sunroom,. Thank you for the great family memories!

Beautiful and comfortable house in a lovely natural setting, five minutes from Pleasant Mountain, which we think is a wonderful family ski area. Marty was very kind and extremely helpful with all our questions and requests. We would love to return and experience other seasons here as well.

Our stay at Jordan’s beautiful place was wonderful. The house is exactly as pictured. The one addition is that along with the kayaks, there are also two paddle boards and a couple of pool noodles. We enjoyed everything from the spacious rooms to the fire pit outside (for s’mores) to the cozy indoor gar fireplace. We had a few questions and a concern during our stay and Jordan was very responsive and hospitable. He even came by to ensure everything was ok. Lastly, the neighbors are incredibly friendly and the neighborhood/lake is quiet and peaceful. Plus it’s about 45 minutes to Freeport (for great shopping) and Portland (for delicious meals). Whether you’re looking for a quick getaway or a longer stay, Jordan’s place is perfect for both couples and families.

We booked Trickey Moose to spend quality time with our two Maine teen grandchildren while they were on spring break. The place was perfect for our needs. The home is quite spacious yet offered each of us an element of privacy. We found the home in immaculate condition and stocked with every essential needed. The “community pantry” was a pleasant surprise and was stocked with the few incidental items we hadn’t brought along. The ping pong and air hockey tables created a friendly competition between the grandkids and grandparents. Great memories were made…. only wish we could have stayed longer.

Had a small bachelorette party here for one of my closest friends. It was the perfect place for a more relaxed girls trip but close enough to get to downtown Portland for any shops, sightseeing, and food! Highly recommended.

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

Great cottage right on the lake! Kayaks were great to take out and explore the lake and see wildlife as well. The cottage is spacious and comfortable. The kitchen is large and well appointed for any cooking you may want to do. Grill and plenty of beach chair/ towels available as well. Adam is extremely responsive and I highly recommend. The place is quite peaceful though the lake gets pretty busy on the weekends with boats but not in an obnoxious way. Loved sipping coffee and reading on the dock each morning. Will definitely book again!

My wife and I stayed at John's place for a quick weekend trip but the house is large enough for several more with 5 additional beds plus some space in the living room for sleeping. Great location on the lake with amazing views and only about a mile and a half from downtown Bridgton with some shops and nice restaurants. The house was immaculate and had everything you need from kitchen accessories to towels to plenty of games and books. John was extremely responsive and I don't think I waited more than 30 minutes for the few back and forth messages we had. Definitely recommend!

We stayed at the cottage for a little celebratory getaway. Although the weather only partially complied, we were amazed by the beautiful views that surrounded the cottage. We spent some time exploring the area and there are some spectacular little gems hidden throughout and around Windham. Maryellen and Bryan were so sweet and made sure to make this stay feel a little closer to home. Definitely a “don’t miss” property!

Steve and Desni's Lakefront home was spectacular! The lakefront views were stunning. The house was as described and provided everything we needed for a wonderful family vacation. Was very clean and tidy upon arrival. Room layouts provided ample space for our group of 10 (could have fit a couple more comfortably) and included all the amenities for indoor and outdoor fun! Zero complaints or cons for renting their home. Would highly recommend it.

What an awesome airbnb! The views are stunning and surroundings couldn’t have been more peaceful. The cottage itself was exceptional and had everything I needed and more. Wish I could've stayed there longer! 10/10 would recommend this place to anyone!

A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

Perfect for what we needed for a weekend getaway. So peaceful and a lot of interesting wildlife. We saw so many different types of birds! The hot tub is spacious and easy to use.

We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!

when we arrived we passed through the front door straight out the back porch door and 30 feet later just gazed across the lake. We knew that instant we were in for an amazing time . Kristin and her husband Dave were great host, don't miss out on this gem when you need to get away from everyday chaos.

Beautiful place. Lovely decorated. I would say that it is probably a little expensive for staying there in the winter/ fall time. Only one of us could sit on the couch at a time due to its location by the tv. The shower is really small and there is no room for toiletries in the bathroom at all. There is a rack but I had to keep all my bathroom stuff in bags the entire time because it is just lacking in space. I would think The price is worth it if you’re staying there in the summer and get to use the lake.

Wonderful Stay in a Great Location! Zak and Emily’s house was exactly as described. It has a fully equipped kitchen, a grill, and a fire pit outside, making it perfect for relaxing evenings. The house is stocked with towels and other essentials, so we had everything we needed. There’s also a ping pong table, which was a lot of fun, and a great collection of movies for entertainment. Check-in was super easy, and the house is conveniently located across from Crystal Lake, offering a peaceful and scenic setting. Communication with Zak and Emily was excellent—they responded quickly and were very accommodating. Overall, it was a fantastic experience, and I would highly recommend staying here for a peaceful getaway. Thanks again, Zak and Emily!

We absolutely loved our stay at Alexa’s cabin. We enjoyed the hot tub, fully stocked kitchen, and truly felt like we could disconnect from the world to connect with those around us. Alexa was a great communicator, provided detailed instructions and local recommendations that were spot on. Don’t hesitate to book this Bridgton escape!

Staying at Braden's camp cabin was great! We enjoyed using the indoor wood-burning fireplace and sitting out on the porch. It was colder this weekend than we anticipated, but the heating worked well in the bunk house and we were able to stay cozy. Would recommend staying here for a simple, no-frills kind of experience.

We loved our stay, the cabin was exactly what we were looking for: private, quiet and an escape from work demands. We especially enjoyed the outdoor space and close proximity to the river, and the screened in porch was simply wonderful to relax and read in. We would love to visit the area again.

Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.