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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

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, 96 reviews

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

ShaunaRating, 5 stars2 months ago
The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.
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
Home in Wakefield
4.96 out of 5 average rating, 28 reviews

In the Trees - NH w/ Lake Access

AmyRating, 5 stars6 days ago
We had a wonderful stay at this cozy, comfortable, and peaceful home—perfect for our family of five! The space was quiet, private, and truly felt like a home away from home. It's in a beautiful location right by Lake Province, and we had almost everything we needed for our 3-night Easter weekend stay. Our older children attend UNH, and this was the perfect spot for us all to be together, relax, play games, and enjoy quality family time. We love to cook, and the brand new kitchen was gorgeous and a joy to use—we prepared three amazing meals together! Just a heads-up for fellow cooks: the kitchen is stocked with the basics, so if you're planning more elaborate meals, you might want to bring a few extra tools. The outdoor space was also a highlight! With beautiful weather all three days, we spent a lot of time outside enjoying the fire pit, string lights, grilling, eating al fresco, and just being together. We truly loved our stay and are already looking forward to coming back.
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, 120 reviews

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

MicheleRating, 5 stars3 months ago
Great place to stay. Winter months are definitely quiet, not a bad thing! I would stay here again.
Guest favorite
Home in Shapleigh
4.96 out of 5 average rating, 145 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

CarlyRating, 5 stars4 weeks 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 stars5 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, 125 reviews

“Stay Awhile in the Lake's Region”

NetanyaRating, 5 stars1 month ago
I reached out to Bob about allowing one of my company crews to stay at his home, he allowed it which was awesome! The home was just as described, the crew were able to relax after working at a jobsite in the area and really enjoyed the home and the area. Bob was very responsive and easy to talk to. I will definitely be booking with Bob again when the crew needs to go back to the job site!
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, 332 reviews

20ft from the Water with Mountain View!

HannahRating, 5 stars2 weeks ago
Such a beautiful and cozy stay! literally feet from the water. It was incredible to wake up to that view. A cozy cabin feel with modern amenities. such a great space! thank you for having us
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 stars1 week ago
It was overall a tremendous experience. I would definitely recommend it!
Guest favorite
Double glass doors open to a view of the serene lakeside, framed by trees. A light-colored, airy interior features a small dining area with white chairs, a cozy seating space, and textured rugs. The natural light enhances the welcoming atmosphere of the space.
Cottage in Standish
4.92 out of 5 average rating, 118 reviews

Peaceful Lakeside Maine Retreat

SarahRating, 5 stars5 months ago
The home was in a beautiful location and it was so peaceful to wake up and look out over the water. The beds were comfortable and there was lots of space for our group to hang out. The host was very accommodating and answered all our questions quickly. Highly recommend!
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 stars2 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.
Top 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!
Top guest favorite
Cottage in Gilmanton
4.96 out of 5 average rating, 112 reviews

Private Beach, Lake Front, Family Friendly Cottage

RichardRating, 5 stars6 months ago
Loved the place. Would definitely try to visit again!

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
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
4.91 out of 5 average rating, 129 reviews

Bear Cabin

StephanieRating, 5 stars1 month ago
The cabin was so beautiful and peaceful. The area wasn't too far from everything, location amazing. It was very quiet and just what we needed to reset. I definitely recommend if you are looking to get away and want to be close to North Conway. The pictures were exactly what you will see when you get there. Absolutely no complaints on our stay at the cabin. We enjoyed the pool table, the dart board and hot tub. We didn't get to light a fire outside which would have been nice but we ran out of time, still very much enjoyed the area. Friendly neighbors while driving through the road.
Guest favorite
Cabin in Parsonsfield
4.96 out of 5 average rating, 220 reviews

Riverfront cabin between Portland & White Mtns.

JennyRating, 5 stars2 weeks ago
What a beautiful thoughtful place! There were games to enjoy, a kayak, a wood stove inside, and fire pit outside. This place was such a beautiful gem!
Guest favorite
The spacious main floor features a rustic log cabin design with a central dining table surrounded by black chairs. A well-equipped kitchen showcases wooden cabinets and a large stove, while a cozy seating area is visible in the background, accented by natural light from nearby windows.
Cabin in Wakefield
4.97 out of 5 average rating, 246 reviews

Beautiful Log Cabin on Belleau Lake -2900 sqft!

JoeRating, 5 stars2 months ago
The cabin on Belleau Lake was perfect for the Ice Fishing trip we did. Cabin was comfortable and lake was easy to access. Had an issue when we first got there but Julie responded right away and quickly resolved it. Overall the group had a lot of fun would definitely stay there again.

Quick stats about vacation rentals with a kayak in Madison

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ477 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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