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Vacation rentals with a kayak in Madison

Find and book unique kayak rentals on Airbnb

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Popular amenities for Madison kayak rentals

House rentals with a kayak

Guest favorite
A two-story home is shown, featuring a beige and blue exterior. The front door, painted yellow, is complemented by a small balcony above. A garage door is visible on the left, while a decorative stone wall outlines the property. The surrounding area is wooded, adding privacy.
Home in Moultonborough
4.96 out of 5 average rating, 68 reviews

Funky Lake House

JulioRating, 5 stars1 month ago
We had a great time at Laurie’s place. Highly recommended and hopefully we will be back soon. Thanks !
Superhost
A deck features white railings and a blue umbrella, providing shade over a seating area. Detailed architecture is showcased by a sloped roof and tall windows, with views of the wooded surroundings and lake visible in the background.
Home in Tamworth
4.82 out of 5 average rating, 97 reviews

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

KarenRating, 5 stars3 days ago
We had a wonderful time. The house was perfect. It was a short walk to the lake. Very peaceful and quiet. Loved having 3 full bathrooms. It was a short drive to Conway for shopping and restaurants.
Top guest favorite
A wooden deck extends alongside the house, bordered by trees and greenery. Outdoor seating is arranged for relaxation, with the tranquil waters of the lake visible in the background. Soft evening light illuminates the scene, enhancing the connection to nature.
Home in Norway
4.99 out of 5 average rating, 83 reviews

Open concept 4 bedroom Lakehouse

ErikRating, 5 stars1 month ago
Great winter weekend stay in Maine, the house was very cozy and perfect for our group. The location is perfect for access to the ski mountains and the town as well. Overall highly recommend Roman’s place, I’m sure it is just as beautiful in the summer!
Guest favorite
An aerial view captures a spacious home nestled among tall trees on the edge of Balch Lake. Two private docks are visible along the shoreline, complemented by a grassy area that leads to a sandy beach. The calm water reflects the surrounding greenery.
Home in Newfield
4.97 out of 5 average rating, 30 reviews

Peaceful 4 bedroom lakehouse retreat

JessicaRating, 5 stars3 months ago
We had a fantastic time staying at Justin’s home!
Superhost
A view from the deck overlooks a tranquil river, framed by a large tree. A picnic table is positioned on the grassy area, with a pergola visible in the background. Snow patches contrast with the green grass, and colorful houses are reflected in the water.
Home in Laconia
4.92 out of 5 average rating, 239 reviews

Waterfront with Game Room Pergola Firepit Downtown

AmberRating, 5 stars2 months ago
The bed was so comfy! We had so much fun with the game room. It was such a cool addition
Superhost
Home in Barnstead
4.89 out of 5 average rating, 121 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AdamRating, 5 stars2 months ago
Great house, quiet and peaceful. Ivars was very responsive. Enjoyed our stay!
Guest favorite
Home in Shapleigh
4.96 out of 5 average rating, 146 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

CarlyRating, 5 stars1 month ago
We had a wonderful stay at this home for a mother daughter weekend end of March. Great location for each of us coming from different states in New England. The home was very clean, each of us commented on how comfortable the beds were, also loved the good quality linens. The huge dining table was unique for a rental and was awesome for sharing meals and doing arts & crafts. Lots of space and seating in the living room as well. Highly recommend staying here!
Guest favorite
Two blue kayaks are positioned on a wooden dock, with calm water reflecting the greenery of trees lining the shoreline. The sky is partly cloudy, adding a gentle contrast to the tranquil setting.
Home in Sanford
4.88 out of 5 average rating, 40 reviews

Waterfront Condo- Maine village retreat

DiannaRating, 5 stars6 months ago
We had a great stay! Loved the views and hot tub. It was so close to town but felt private with the privacy fence. Owners were very responsive! Thanks for a great stay

Cottage rentals with a kayak

Superhost
A serene lakeside view showcases a small, wooden dock extending into the calm water. Two red kayaks rest on the grassy edge, surrounded by lush greenery and gentle hills in the background. Soft pastel hues of the sky hint at dusk.
Cottage in Conway
4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

TeraRating, 5 stars6 months ago
This place was really nice! Its on a beautiful lake with a lot to do! Jessica had plenty of kayaks, canoes, and life vests. The surrounding is beautiful and peaceful. The location is great with plenty of restaurants and shopping nearby. It's also very close to many great hiking areas Mt Washington.
Top guest favorite
A comfortable living area features a gray sofa and two armchairs, arranged around a round wooden coffee table. Light streams in through two windows, illuminating a neutral-colored area rug. Two lamps provide additional soft lighting, enhancing the inviting atmosphere.
Cottage in Alton
4.98 out of 5 average rating, 126 reviews

“Stay Awhile in the Lake's Region”

NetanyaRating, 5 stars3 weeks ago
Bob and Jo are such amazing hosts. This is our second stay at their home within 3 weeks and plan to book again. They check in to make sure the check ins go well and always ask if there is anything that is needed. Their response time is so quick and communication is very easy. Their home is amazing and we plan to book with them again.
Guest favorite
A serene lakeside view captures a white two-story house surrounded by tall trees and lush greenery. The lake reflects the blue sky with a few clouds, and a glimpse of a boat can be seen near the shore, emphasizing the tranquil environment.
Cottage in Windham
4.82 out of 5 average rating, 138 reviews

Cozy camp near highland lake

TyRating, 5 stars1 week ago
My stay here was absolutely awesome—cozy, charming, and full of thoughtful touches that made it feel like a home away from home. Tucked away in a quiet spot, it had just the right mix of comfort and style, with a super comfy bed, a well-equipped little kitchen, and warm lighting that made evenings feel magical. The host went above and beyond, leaving local tips and a welcome treat that totally made my day. I honestly didn’t want to leave! And the view to the lake was so beautiful especially the sunsets for the cabin overlooking everything was just so awesome!
Guest favorite
A cozy cottage is depicted by the pond, surrounded by tall trees that reflect beautifully on the water's surface. The structure features large windows and a welcoming porch, providing a serene atmosphere amidst nature. Soft light enhances the tranquil setting.
Cottage in Conway
4.95 out of 5 average rating, 333 reviews

20ft from the Water with Mountain View!

ElizabethRating, 5 stars2 weeks ago
my partner and i stayed here to just get away from reality for a couple days! this lakeside cottage is the perfect place to do so. we couldn’t decide if we wanted to go out and about or stay right in the cabin, it was so peaceful! thank you for hosting!
Superhost
A bright, open kitchen and living area is designed with large windows allowing natural light. A central island with chairs offers space for dining or socializing. A comfortable seating area is visible, complemented by warm wood accents and serene artwork on the walls.
Cottage in Lyman
4.82 out of 5 average rating, 101 reviews

RK North : All season Waterfront cottage with dock

BrianRating, 5 stars2 weeks ago
It was overall a tremendous experience. I would definitely recommend it!
Guest favorite
A serene lakefront view showcases a cozy cottage surrounded by lush trees displaying vibrant autumn colors. The still water reflects the landscape, enhancing the tranquil scene of nature. Gentle ripples and scattered rocks can be seen along the shoreline.
Cottage in Whitefield
4.96 out of 5 average rating, 239 reviews

Private Pond Escape: Luxe Cottage/Private Isle

KimberlyRating, 5 stars3 weeks ago
This place is the perfect reminder of the kind of place you wish to retire at. I can’t wait to come in the summer or fall! Interestingly enough we came during April snow weather and still had the best and most relaxing time. It was a huge plus that Cumberland farms was two minutes away and a lot of other local stores were around. Extremely dog friendly and truth be told any dog’s favorite place this would easily be. I brought my puppy and it was a great way to expose him to ALOT. Mary was so responsive and helpful and we actually got stuck in the mud and her whole family plowed us out and we got a laugh at the end as well in the midst of it all. The place was clean, you really felt at home with all amenities that were included, I would just keep in mind there was not a kitchen aide mixer so bring a handheld mixer and that would do the trick depending on what you’re planning on baking but I was able to make a lot of things without. Highly recommend, very peaceful, and all you need.
Guest favorite
Two kayaks, one yellow and one blue, are positioned side by side on a calm riverbank. The surface of the water reflects the overcast sky and surrounding trees, creating a serene scene perfect for outdoor activities.
Cottage in Buxton
4.98 out of 5 average rating, 142 reviews

Peaceful Cottage on Maine Flower Farm

RaeganRating, 5 stars6 months ago
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!
Guest favorite
The lakeside cottage features a welcoming exterior surrounded by lush greenery. A spacious deck with colorful furniture overlooks the water. A private dock is visible, with adirondack chairs positioned for relaxation, inviting guests to enjoy the serene lakeside setting.
Cottage in Middleton
4.96 out of 5 average rating, 184 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

CourtneyRating, 5 stars1 week ago
My family and I had such a WONDERFUL long weekened away at Fox & Loon! It was so relaxing and peaceful, and exactly what we needed! The house was the perfect setup for our family of 4. It was so open and bright, and had everything we needed. We got tons of use out of the hot tub, and fished every day from the dock! The sunsets were gorgeous! Sheri and Adam were the perfect hosts! Right from the beginning, they were extremely responsive and answered every question I had (which was a lot!). They even went out of their way to find out some additional information I requested. We would absolutely, without a doubt, stay here again! Thank you Sheri and Adam!

Cabin rentals with a kayak

Guest favorite
Two kayaks are stored vertically on a wooden shed, with one being a light orange color and the other yellow. Lush greenery surrounds the structure, emphasizing a natural setting. The shed features a white garage door and a metal roof, blending harmoniously with the landscape.
Cabin in Woodstock
4.96 out of 5 average rating, 153 reviews

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub

JenavieveRating, 5 stars1 month ago
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!
Guest favorite
The lakefront cabin is nestled among lush greenery, elevated on a wooden deck overlooking the water. Smooth stones lead down to the lake, with light filtering through the trees, creating a serene atmosphere in this natural setting.
Cabin in Andover
4.95 out of 5 average rating, 113 reviews

Little House on the Lake in the Forest

AnthonyRating, 5 stars2 months ago
Im not someone of many words, but it was an unbelievably cozy and wonderful experience
Top guest favorite
A private dock extends over calm waters, surrounded by vibrant autumn foliage. A flag is displayed proudly atop the dock, which features a ladder for easy access to the lake. Reflections of trees are visible on the water's surface.
Cabin in Oxford
4.94 out of 5 average rating, 132 reviews

Thompson Lake, No Cleaning Fee Pine Point Cottage,

BeatriceRating, 5 stars6 days ago
Mike & Kathy are the perfect hosts (hands down), they are easy to get in touch with, fair & very welcoming. Would hundred percent recommend them and their place. Awesome lake front property!!!
Superhost
A blue kayak is positioned alongside the cabin's exterior, with paddles resting above it. Various life jackets are hung nearby, showcasing bright colors. The surroundings are shaded by tall trees, creating a natural setting for outdoor activities.
Cabin in Raymond
4.93 out of 5 average rating, 154 reviews

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

WaltRating, 5 stars6 months ago
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!
Guest favorite
An aerial view captures the serene surroundings near Crystal Lake, showcasing a tree-lined road bordering the water. A private dock is visible, along with lush green foliage emphasizing the natural beauty of the area.
Cabin in Harrison
4.99 out of 5 average rating, 125 reviews

Get away at Crystal Lake

GabrielRating, 5 stars3 months ago
Great cabin, location, and hosts. Our group had a great time coming back for our second trip here and would highly recommend. 5 stars all around.
Guest favorite
Cabin in Bridgton
4.93 out of 5 average rating, 123 reviews

Private cabin w hot tub,skiing,firepit & mountains

DanRating, 5 stars2 weeks ago
This is a beautiful home that is very well maintained and cared for. Alexa's cabin was a great place for 5 of us to gather, relax, and enjoy. Kitchen has everything you need, the hot tub is fantastic during a spring snowstorm, the beds were very comfortable, and it provided ample space for us.
Guest favorite
A wooden deck features a small round table surrounded by two black metal chairs. The serene view of a pond is visible in the background, framed by trees and a grassy area, creating a peaceful outdoor space.
Cabin in Madison
4.92 out of 5 average rating, 130 reviews

Bear Cabin

LilaRating, 5 stars1 month ago
Absolutely beautiful and peaceful stay. John and Cassie’s cabin was just as described and exactly what we were looking for. We drove up during a snow storm but the roads were plowed and well maintained. Very isolated and private but never felt unsafe or uncomfortable. Not too far from things to do but we were content enjoying the cozy relaxing home. John was quick to communicate with us if we needed anything and was very helpful.
Guest favorite
Cabin in Parsonsfield
4.96 out of 5 average rating, 222 reviews

Riverfront cabin between Portland & White Mtns.

ColinRating, 5 stars6 days ago
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

Quick stats about vacation rentals with a kayak in Madison

  • Total rentals

    20 properties

  • Nightly prices starting at

    $130 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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