Holiday rentals with a kayak in Madison

We had the most amazing stay at this Ossipee Airbnb! The barn space and game room were such a unique and fun addition—perfect for hanging out in the evenings. The property is right on the pond, which made for the most peaceful mornings and gorgeous sunset paddles. We loved having the kayaks available—it made getting out on the water super easy and so much fun. Inside, the home was spotless and incredibly well-stocked with everything we needed, from kitchen essentials to extra blankets. You can tell a lot of thought has gone into making guests feel comfortable. Michael and Randle were incredibly responsive and helpful hosts. And the huge Blackstone grill was great for our party—we cooked outside while soaking in the view. One night we got Pizza Barn as hosts recommended because it was featured on Phantom Gourmet… yum! Whether you’re fishing off the dock or just relaxing by the fire, this place is the perfect peaceful getaway. We can’t wait to come back!

a wonderful place to stay.

My family loved this house! The property is absolutely gorgeous! We enjoyed being close to Conway, but out of the crowds and traffic. The layout of the house gave everyone their own space, while also offering the downstairs area where we could all sit together and watch TV or play ping pong. The house feels very homey and welcoming--lots of cute touches. Even before we left, we were all talking about renting this house again next year, but for longer next time, so we could fully enjoy the pool, tennis court and lovely deck! Highly recommend!!

This remote Cabin was perfect for us. We were looking for a comfortable place to stay for the weekend with announced rainfall. It was spacious, warm and had everything we needed. We can highly recommend this place.

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.

The house is awesome: lake view, lake direct access, large kitchens, someone plowed the driveway after the snow storms. We had a great stay, did ice skating on the lake, kings pine ski center is family friendly.

We had a fantastic time staying at Justin’s home!

We would definitely go back for another stay. Carl is a wonderful host and was very responsive and helpful. The house is beautiful and is located in such a tranquil and scenic location. We are a family of 6 along with our black lab and everyone fit comfortably. I highly recommend this place for a family get away.

We had a great time at Robert’s place. The home has everything you could want, and there are plenty of things to do in the area. It was a great home base for our weekend! The kids loved the game room!

They were accommodating, flexible, and very gracious. They had an entire binder of information with details about where to find fans, towels, flashlights, how to work the shower, heat, grill, and about anything else you can think of. It also had emergency services, restaurants, places to have a good time, and good details about checkout expectations. Overall we were extremely happy with the property and our stay, and were honored by the personalization they did for us specifically as it was our Honeymoon and they wrote us a custom note by hand for when we arrived. Highly Recommended - Will Rent Again!

The cottage was an excellent place to stay, a clean comfy environment with a wonderful yard.

I had a nice stay at Alexa's. It's beautiful, quiet and ideal to get some rest while being surronded with nature. The best!

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

Janet’s place in Standish was great and we could not have asked for a better host. Apart from the home itself, Janet was very friendly and responsive. She even proactively offered early check in / late check out, extremely unexpected and appreciated! Would absolutely recommend this BNB 10 times out of 10.

My wife and I wanted to have a lakeside getaway to kick off the summer! The weather was a bit colder than we had hoped, so we ended up enjoying the cottage to its fullest, which was a much needed and relaxing stay with everything we needed right there. It was very cozy and the lakeside view was wonderful, especially in the mornings. The owner was also very responsive to messages, making the experience seamless. We hope to visit again!

The cottage was so wonderful! The pictures did not do it justice, we appreciated the welcome bouquet made from her farms flowers! The grounds were so beautiful and peaceful. We wanted a relaxing getaway and that’s exactly what we got. The bed was so comfortable and we enjoyed the kayaks, fire pit, and bird watching! The location was far enough way for the privacy but a close drive to Portland and other must see locations. Jessica was responsive and communicative with any concerns. We cannot wait to come back and visit every season and cannot recommend the cottage enough!

We had a wonderful stay and will definitely return! The cabin is lovely. My daughter enjoyed kayaking around the lake. We also enjoyed the science center, Walter’s basin, and birdwatching. Thank you!

Came for the Fall colors; left in love with the place! Small but delightful. Cluttered in the most fantastical way. Nestled in paradise. Bonnie is so nice and friendly! Pay attention to the fact that the toilet is not attached to house. Short walk to privet and very clean!

What an amazing hosts! When i check in they both came and visited and gave me a grand tour of things of the place. Showed where the lake was to kayak, recommended places to eat, and visited. Michael was quick to respond making sure i was doing great. I would totally go back and rent their place again! Thank you so much!

We had a wonderful stay at Ricky’s cabin on Bear Pond! It was peaceful, with beautiful views of the water, and we loved having campfires in the evenings. The cabin was clean, cozy, and had everything we needed for a relaxing getaway in the Maine woods! Ricky was a great host—friendly, responsive, and made sure we felt right at home. We would highly recommend staying here!

Stayed here for the second time with our family of five, including two toddlers and a baby. The house/property is the perfect setup for us! Everything is safe for kids and on one floor. There are things like pack-and-plays, kid dinnerware, kid toys/books, and sand toys provided. The sandy beach is close enough that our monitor reached from the baby’s room during nap time. Our oldest calls it “the little house” and has been talking about it since the last time we stayed here a year ago. It is the perfect little getaway! 🙂

Had an amazing stay here, so wondering could go fishing at the dock, the basement was so fun to play pong and just hang out, loved being able to watch disney+, just overall a wonderful stay and amazing and friendly people.

This beautiful A-Frame was a perfect weekend getaway. My girlfriend and I spent the weekend here and it was in a great location with perfect accommodations for two people. The place was clean with great amenities (grill, fireplace, etc.) Will definitely be hoping to return in the future / am eager to recommend this property to anyone.

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