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Vacation rentals with a kayak in Winthrop

Find and book unique kayak rentals on Airbnb

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Popular amenities for Winthrop kayak rentals

House rentals with a kayak

Superhost
Home in Acton
4.85 out of 5 average rating, 26 reviews

Private oasis on Lake Mousam all season activities

PeterRating, 5 stars2 months ago
Great house and location. This was my 2nd time staying here and will definitely be coming back again.
Top guest favorite
A vibrant blue kayak is positioned in the foreground, with a wide view of Pleasant Pond stretching into the distance. Calm water reflects the sky above, while lush greenery lines the shores. Cloudy skies create a serene atmosphere perfect for relaxation and exploration.
Home in Gardiner
4.98 out of 5 average rating, 45 reviews

2 Acre Waterfront w/Canoes & Kayaks, Game Room

LivRating, 5 stars1 month ago
I love coming to Maine, and this was my first time staying at Rob's place—it was beautiful! Rob was more than accommodating and incredibly hospitable. The home is gorgeous, super clean, cozy, and very private. The game room was such a fun bonus! It was the perfect little getaway. Thank you so much, Rob, for everything! I will definitely be keeping this place in mind for future visits!
Guest favorite
Home in Fayette
4.9 out of 5 average rating, 21 reviews

Lakehouse with 100ft of private waterfront

GeorgeRating, 5 stars6 months ago
My wife and I spent our first year anniversary in this wonderful home. We had a great time enjoying the fall colors and over looking the beautiful pond, especially in the morning as the fog broke. Within 15 minutes there were several grocery shopping options, restaurants, and breweries. Perfect balance of being in a quiet setting but having amenities nearby. Would recommend and hope to go back next autumn!
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
A serene outdoor space is bordered by trees and features a gravel area with seating around a fire pit. A wooden deck extends from the cabin, providing views of the nearby river, enhancing the natural landscape.
Home in Naples
4.99 out of 5 average rating, 116 reviews

LUX Designer Private Waterfront

ElliosRating, 5 stars1 day ago
Jon’s space was very clean, private, and presented a “wow” factor in every direction I turned. Very well thought out; a truly transformative experience!
Guest favorite
A serene waterfront scene showcases a calm lake surrounded by lush greenery. A small boat rests on a grassy area, inviting relaxation and exploration. The cloudy sky reflects over the water, creating a peaceful atmosphere.
Home in West Gardiner
4.96 out of 5 average rating, 26 reviews

2 BR Waterfront house with stunning view.

KristenRating, 5 stars7 months ago
This was a really nice house on a beautiful lake. The beds were comfortable and there were enough to accommodate us. It was very clean and easy to enjoy your stay. We really enjoyed our stay.
Guest favorite
A log cabin is situated on a grassy expanse beside the water, surrounded by trees displaying vibrant autumn foliage. A private dock extends into the lake, providing access for boating activities, while the spacious lawn offers plenty of room for outdoor enjoyment.
Home in Stetson
4.95 out of 5 average rating, 190 reviews

Lakefront Log Cabin on Pleasant Lake

JoelRating, 5 stars1 week ago
This was our second stay with Devon and as usual it did not disappoint! It is exactly what we needed for a quiet getaway. It is very serene with sounds of the Loons echoing across the lake. Did not see a car or person in 4 days which was great. Devon was always in touch if needed and accommodating. Great kitchen with everything needed for a snack or a full meal. A very relaxing stay!
Top guest favorite
A serene view of a grassy yard leading to a lake, bordered by trees. A sandy beach area is visible, with a wooden dock extending into the water. Two kayaks are situated on the grass, alongside a red paddleboat.
Home in Wakefield
5 out of 5 average rating, 8 reviews

The lake at your back door!

AdrianRating, 5 stars6 months ago
Irene was a great host! She reached out with very helpful information regarding the property and lake, which allowed us to prepare well for our stay. The house was clean, well-stocked, and exactly as pictured—perfect for a vacation getaway with friends!

Cottage rentals with a kayak

Top guest favorite
The exterior of the lakeside cottage is showcased against a clear blue sky, surrounded by lush greenery and tall trees. A spacious lawn leads to the water's edge, with the shimmering lake visible in the background.
Cottage in Belgrade
5 out of 5 average rating, 103 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes Maine

SarahRating, 5 stars5 months ago
This property was awesome we were all very happy with the location, amenities, price and host. Hillary was polite and very helpful. This trip almost didn’t happen as our previous reservation was canceled 12 hours before check in from a different host. Luckily Hillary saved the week with her quick response time and answering questions about sleeping situations etc. would stay here again in a heart beat highly recommend!
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, 136 reviews

Cozy camp near highland lake

TyRating, 5 stars1 day 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, 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
Guest favorite
A serene lakeside setting features three green adirondack chairs arranged around a stone fire pit. The clear waters of Great Pond reflect the blue sky, while a wooden dock extends into the lake, bordered by lush green trees in the background.
Cottage in Belgrade
4.93 out of 5 average rating, 135 reviews

Near Waterville | Lake Great Pond | Dog Friendly

TammyRating, 5 starstoday
The place was beautiful and exactly what we needed! I would definitely recommend staying here.
Guest favorite
A quaint cottage is nestled among vibrant gardens filled with colorful flowers, overlooking Snow Pond. A picnic table is shaded by a large umbrella near the water's edge, while trees provide dappled sunlight on the cottage's exterior.
Cottage in Sidney
4.91 out of 5 average rating, 130 reviews

Waterfront Cottage

AaronRating, 5 stars6 months ago
Amazing place, it was exactly what we needed.
Guest favorite
Two kayaks, one yellow and one orange, rest along a grassy shore next to a calm waterfront. Lush green grasses frame the scene, contrasting with the tranquil blue water and distant shoreline, inviting exploration and connection with nature.
Cottage in Topsham
4.93 out of 5 average rating, 249 reviews

Cozy waterfront home on Merrymeeting Bay.

ElaineRating, 5 stars2 months ago
This is our second stay here and we just love the location. looking out over the river is so relaxing.
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!
Superhost
A wooden dock extends over calm water, leading to a small boat tethered at the side. Lush greenery borders the opposite shore, with a clear sky overhead, dotted with soft clouds.
Cottage in Livermore
4.94 out of 5 average rating, 53 reviews

Loons Rest – Maine Quintessential Cottage

CraigRating, 5 stars7 months ago
Loons Rest was the perfect get away spot for our 40th anniversary. We were lucky to enjoy the swimming dock in mid September as the daytime temperatures were in the upper 70's to low 80's. The lake was pristine and was warm enough for swimming still. We enjoyed watching and hearing the loons as well as the eagles and kingfishers. We loved the outdoor fire pit when the evenings turned cool as well as the indoor fireplace which is a work of art! Also the was plenty of well seasoned firewood. Everything about this place is very well thought out. If they don't have it you don't need it! The kitchen was well equipped and we were happy to find that there was everything we needed to prepare pizzas to cook on our solo stove pizza oven that we had brought along! John is a great host and responded quickly to any questions we had. Would highly recommend Loons Rest to anyone who is looking for a peaceful and relaxing spot to vacation.

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!
Top guest favorite
A kayak is stored on a wooden rack, positioned under a canopy of trees. Sunlight filters through the leaves, casting dappled shadows on the ground. The view of the river, partially obscured by vegetation, can be seen in the background.
Cabin in Dresden
4.95 out of 5 average rating, 184 reviews

McKeen's Riverside Retreat

BettyRating, 5 stars2 months ago
The cabin was just as advertised. A quiet clean space!!
Guest favorite
Cabin in Hope
4.97 out of 5 average rating, 101 reviews

Hobb’s House - Year Round Log Cabin on the Water

MelissaRating, 5 stars6 days ago
Connor was an AMAZING host! From the very beginning, he was always very responsive, and was consistently available to answer my questions promptly. His cabin on the lake was so cozy, it truly felt like our home away from home. It was beautifully decorated, peaceful, serene, well-stocked with anything that one could need. His recommendations were extensive and were very much appreciated. We were celebrating our 30th wedding anniversary and really loved being able to stay there with friends for a few days before departing for another excursion. It gave us time to celebrate and make some great memories with them - something that we will always treasure! The worst thing about this cabin? - Having to leave it in the rearview mirror! Connor, thanks so much for sharing your beautiful cabin with us. You can count on us to be back in the future! Thank you!
Guest favorite
An expansive view of a tranquil lake is presented, with a wooden dock extending into the water. Trees frame the scene, displaying colorful autumn foliage. The sky is clear, reflecting calming blues and whites, while mist lightly rises from the surface of the lake.
Cabin in Madison
4.85 out of 5 average rating, 130 reviews

Charming cottage at the Lake!

KatherineRating, 5 stars7 months ago
Charming little cottage on the lake! Had a lot of fun, easy to get to town and the lake was serene and peaceful. Great place to stay!
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
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.
Top guest favorite
A handcrafted log cabin is set among tall trees, featuring a bright orange exterior and green trim. A screened porch offers a view of the nearby water. A sandy area in front of the cabin provides outdoor space for leisure, blending naturally with the surrounding landscape.
Cabin in Weld
4.94 out of 5 average rating, 108 reviews

Camp Bai Yuka/Little Camp (Log Cabin on Webb Lake)

RonniRating, 5 stars6 months ago
We celebrated our 25th wedding anniversary at this charming camp on Webb Lake, and it was everything we hoped for and more. The serene setting was perfect for enjoying the outdoors together. We spent our time fishing on the beautiful lake, where we caught a handful of fish. Kayaking was a highlight as well; the combination of being on the lake, mountain views and beautiful weather was simply magical. The camp itself was cozy and well-equipped, providing a wonderful weekend getaway. If you're looking for a peaceful getaway filled with outdoor fall activities, this is the place to be. We left already planning out next trip back. Thank you for sharing your home.

Quick stats about vacation rentals with a kayak in Winthrop

  • Total rentals

    20 properties

  • Nightly prices starting at

    $90 before taxes and fees

  • Total number of reviews

    920 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Kennebec County
  5. Winthrop
  6. Rentals with a kayak