
Holiday rentals with a kayak in Madison
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Top-rated Accommodation with a Kayak in Madison
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Holiday House Rentals with a Kayak

Hot Tub | Waterfront | Mt. View | Game Room | Luxe
We stayed at this home for our wedding weekend and were genuinely impressed. Everything was clean, comfortable, and thoughtfully stocked. The hot tub heated quickly and worked great, the showers had excellent water pressure, and there were practical extras throughout the house like hair ties, toiletries, and more than enough towels. The house was cozy and every detail felt well-considered. We’re already talking about coming back for a future trip. This was the perfect place to stay.

Waterfront Gem walkable to Restaurants!
a wonderful place to stay.

Beautiful 4 season mountain retreat
We enjoyed our stay. Jill was easy to communicate with and flexible with us. The home felt like home and she has a lot of amenities that they offer for those that stay . It was clean and comfortable .

Secluded cozy family retreat, dog friendly!
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!!

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
We had an absolutely wonderful time at Julie's lakeside home for Father’s Day weekend. The setting was serene, with beautiful views of the water, making it the perfect spot to relax and enjoy quality time together. The home was well-equipped and comfortable, offering everything we needed for a memorable stay. Julie was a fantastic host, ensuring that our experience was seamless and enjoyable. We truly appreciated the peaceful ambiance and thoughtful touches throughout the space. Highly recommend for anyone looking for a lakeside retreat!"

Beautiful Three Bedroom Home with Incredible View
Staying at this home was a wonderful experience. The house was in pristine condition, with everything clean and organized. The view was breathtaking and the photos on AirBnb represented the home well. Brittany was responsive and helpful, on-top of being kind and understanding. The coffee station was a real plus! We greatly enjoyed our stay and would return if possible.

Kayak to the Causeway-50s cottage with modern vibe
This has been by far the nicest place we have stayed. Super clean and nicely decorated. Wonderful communication by the hosts. Perfect weekend getaway.

Hot Tub Haven: Dog-Friendly Retreat
Abbey’s place was amazing for a birthday getaway! Stayed with some friends and there was enough space for all of us. Felt right at home! Space looked just like the photos & Abbey was VERY quick to respond to any questions we had! Would recommend!
Cottages with a kayak

“Stay Awhile in the Lake's Region”
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!

Lovely cottage on Sunrise Lake, Middleton, NH.
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!

Completely updated detached cottage/Paugus Bay!
We enjoyed a great weekend getaway at this place. Denise was a great host who were helpful and always quick to respond. The house is cozy and clean, perfect size for two adults. It is conveniently located while being private. We kayaked on Paugus Bay and hiked Mt Major. Would definitely come back again.

Cottage with antique charm view & river HSI Wi-Fi
The cottage was an excellent place to stay, a clean comfy environment with a wonderful yard.

RK North : All season Waterfront cottage with dock
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

Peaceful Lakeside Maine Retreat
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.

Peaceful Cottage on Maine Flower Farm
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!

Beautiful Lakeside Cottage
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!
Cabin rentals with a kayak

Beautiful private cabin on Big Squam Lake
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!

Rustic, cozy cabin on Sebago Lake. A hidden gem.
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!

Thompson Lake, No Cleaning Fee Pine Point Cottage,
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!

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views
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! 🙂

Lakeside Cabin Nestled in the Pines
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.

Get away at Crystal 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!

Breezy Moose - A Frame Cabin/ Pet friendly
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.

Maine Lakes-Pleasant Mt-Private Trails
Third visit in three years for a weekend fishing getaway. Great location, beautiful property. Excellent hosts. Looking forward to a return visit.
Quick stats about holiday rentals with a kayak in Madison
Total rentals
20 properties
Nightly prices starting at
$216 NZD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Sebago Lake
- Squam Lake
- Scarborough Beach
- Sunday River Resort
- Story Land
- Loon Mountain Resort
- Attitash Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Surfside Beach
- Franconia Notch State Park
- Fox Ridge Golf Club
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Cannon Mountain Ski Resort
- Palace Playland
- Ferry Beach
- Cliff House Beach
- King Pine Ski Area
- Purity Spring Resort
- Diana's Baths
- Dartmouth Skiway
- Dunegrass Golf Club