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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

Guest favorite
Home in Newport
4.94 out of 5 average rating, 126 reviews

Sugarmaple Lakehouse - Sebasticook Lake Newport ME

DanielleRating, 5 stars1 week ago
Great location. Woke up to the sounds of birds. very responsive. I would have given it a 5 star all the way, David was amazing and responded in a very timely manner. But, the turn over service could have been much better. The previous guest left a wine bottle in the automatic fridge ice dispenser and it was unfounded until my family found a large peice of glass in their drink, serious hazard to drink glass. Should have been spotted by the turn over service but, who would check the ice maker for a bottle a wine? I understand that. Very uncommon and unfortunate for us. David responded in a very fast manner and gave us options to accommodate the situation. I would have left a 5 star if this was the only thing but everything was so unorganized in the kitchen, they had everything but nothing made sense to why it was there. Sink didn't drain. There were also stains on the sheets and a pizza box left by the fridge that wasn't ours. Little things but the turn over service was a let down.
Top guest favorite
A scenic view of a wide body of water reflects sunlight, surrounded by trees. The exterior of the home showcases a spacious deck, overlooking a lush green lawn. The interior features a vaulted wood ceiling and a game room with air hockey and tables. The deck is adorned with comfortable chairs.
Home in Gardiner
4.98 out of 5 average rating, 46 reviews

2 Acre Waterfront w/Canoes & Kayaks, Game Room

BrianRating, 5 stars1 month ago
If you want a private, well furnished home in the woods with fishing access on the stream and 2 fire pits this is your place!! Staying at this house made a work trip for my crew and I, feel like we were on vacation for 2 nights while staying there. Worth the money and great hosts!
Top guest favorite
Home in Windham
4.94 out of 5 average rating, 140 reviews

Waterfront Gem walkable to Restaurants!

LinhRating, 5 stars1 week ago
It’s very cute little house. We’re enjoy it. Thank you so much.
Superhost
The image showcases a serene lake view framed by colorful autumn trees, their leaves in shades of red and yellow. A sandy area is visible with a fire pit and several chairs arranged nearby, along with a glimpse of canoes at the water's edge.
Home in Greenwood
4.96 out of 5 average rating, 111 reviews

Lakefront summer getaway cabin for 6

LezlieRating, 5 stars1 week ago
We had a great week at the cabin! The view is amazing and it was so relaxing. Courtney was very responsive and attentive. Highly recommend for a cozy getaway in a beautiful setting.
Guest favorite
Home in Belgrade
4.86 out of 5 average rating, 21 reviews

Family's Paradise: 3BR/2BA,Game Room & Lake Access

AnthonyRating, 5 stars3 months ago
Great rental property in a great place.
Superhost
The exterior of the home is shown from the water, surrounded by trees displaying vibrant autumn foliage. The house features multiple windows and a large deck that leads to stairs sloping down to the water's edge. The reflection of the house and trees can be seen on the calm water surface.
Home in Pittsfield
4.82 out of 5 average rating, 124 reviews

Cozy Waterfront Home With Breathtaking Views!!!

JessicaRating, 5 stars3 days ago
We had an amazing time. TJ was very responsive and gave his secrets for fishing! He also accommodated a request that was an overlook on my part. I can’t say enough good things about the place itself or how nice TJ was. It was a phenomenal experience all around!
Top guest favorite
Home in Bath
5 out of 5 average rating, 104 reviews

Waterfront Farmhouse with Modern Flair!

BrendanRating, 5 stars2 weeks ago
We loved our stay (late May, 2025). The weather did not cooperate but the house was perfect. Thank you Debbi!
Top guest favorite
Home in Newcastle
4.99 out of 5 average rating, 159 reviews

Peaceful Oasis by the Great Salt Bay - 3BR/2Ba

RandyRating, 5 stars2 weeks ago
My wife and I completely enjoyed our stay at Ani’s place. She literally thought of everything any guest could ever want. Beautiful surroundings…walking distance to the Fish Ladder….a couple of miles to all the restaurants downtown. And the place itself is immaculate. The kitchen was perfect for eating in every night. This place is an absolute no-brainer to rent and we can’t wait to return!!!

Cottage rentals with a kayak

Guest favorite
A view of Tracy Pond is framed by the cottage's window. Lush trees with vibrant autumn foliage border the serene water's edge, reflecting a peaceful landscape. The clear sky above enhances the natural beauty of the secluded environment.
Cottage in Hermon
4.93 out of 5 average rating, 108 reviews

Lakefront Cottage on Tracy Pond, New Hampshire

AnBinhRating, 5 stars3 days ago
Anna was incredibly communicative and her place was clean, quiet, and exactly what we were looking for. We especially loved her two little greeter cats!
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, 105 reviews

Lakefront Home, Sandy Beach, Belgrade Lakes, Colby

ShonaRating, 5 stars1 month ago
Hillary's home was so cozy, beautiful, and just overall a wonderful place to visit. Beds super comfortable. Kitchen had everything you need and more. The view of the lake was so beautiful. I could go on and on.... Hillary is so easy to get along with. Answers all questions and gives great advice of the area and things to do and see. Overall Fantastic! Christ's local convience store has everything!! Our stay was terrific.
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
4.94 out of 5 average rating, 345 reviews

20ft from the Water with Mountain View!

AlisonRating, 5 stars4 days ago
Loved our stay at this peaceful lake. The house is perfect- cozy and has everything you need. We loved paddleboarding and the access to cute downtown North Conway is ideal!
Top guest favorite
A cozy cabin is nestled among towering trees, surrounded by a natural landscape. A gravel path leads to the entrance, where wooden steps are visible. The warm exterior contrasts gently with the cool tones of the forest.
Cottage in St. George
4.96 out of 5 average rating, 231 reviews

Hidden Haven A Rustic Retreat In St. George, Maine

JoelRating, 5 stars2 weeks ago
Really enjoyed our stay at the cottage. Everything was clean and cozy. Great time going through the DVDs, board games, and close access to Rockland town. This was an amazing stay and one for the scrap books!
Guest favorite
A collection of five kayaks and one canoe is positioned along the shore, next to tall grasses. The vibrant colors of the kayaks contrast against the calm water of Merrymeeting Bay. The serene landscape is framed by trees in the background, illustrating a peaceful outdoor setting.
Cottage in Topsham
4.93 out of 5 average rating, 253 reviews

Cozy waterfront home on Merrymeeting Bay.

EmilyRating, 5 stars1 week ago
Loved our time here! It’s about a 40 minute drive from Portland and then 5-10 from Brunswick. The neighborhood is quiet and perfect, exactly what we needed to relax! We loved coming back from Portland and grabbing dinner and gelato in Brunswick, such a nice way to unwind from a long day. Highly recommend and would love to stay here again :)
Top guest favorite
A deck area features two green Adirondack chairs positioned to face the tranquil waters of East Pond. Natural greenery from surrounding trees provides a sense of privacy, enhancing a peaceful atmosphere for relaxation by the lake.
Cottage in Oakland
5 out of 5 average rating, 120 reviews

The Rocky Road Camp on East Pond

CharlesRating, 5 stars1 month ago
Two things stood out to us: Tim and Melissa were fantastic hosts. Responsive, flexible, and went out of their way to make us feel at home. If anything, they kind of undersell the lakeshore. Beautiful, peaceful, and a large area. We were here too early in the season to take full advantage, but this must be heaven in the summer. Hope to come back during kayaking season.
Guest favorite
A single-story cottage is shown with a white wooden exterior and a grey roof. Multiple windows with a dark trim allow natural light in. A gravel pathway leads to the entrance, where a door is framed by steps. A dog rests on the grass nearby.
Cottage in Buxton
4.97 out of 5 average rating, 144 reviews

Peaceful Cottage on Maine Flower Farm

RaeganRating, 5 stars8 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!
Superhost
A serene view of a lake surrounded by trees, reflecting the clear blue sky. The water's surface appears smooth, indicating calm conditions. The landscape features distant houses among the trees, contributing to a peaceful natural setting.
Cottage in Freedom
4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Leigh AnnRating, 5 stars3 weeks ago
Helen was actually wonderful. She returned calls and everything. It was a great place to stay beautiful and hope to stay there again someday.

Cabin rentals with a kayak

Guest favorite
Cabin in Strong
4.91 out of 5 average rating, 140 reviews

Lakefront Stunning Home, just 35 min to Sugarloaf!

ChangchiRating, 5 stars2 months ago
Absolutely beautiful views. Peaceful location. House is very well equipped with board games and basic amenities!
Guest favorite
The rustic cabin is nestled among towering trees, featuring a stone chimney and a wooden deck adorned with green chairs. A covered porch offers protection from the elements, while the natural surroundings create a serene atmosphere.
Cabin in China
4.89 out of 5 average rating, 177 reviews

Rustic Family Cabin on China Lake

JamesRating, 5 stars5 days ago
We come every year. It’s a great quiet place.
Top guest favorite
The dining area features a round table surrounded by wooden chairs, illuminated by a hanging light fixture. A small television is mounted on the wall, providing entertainment. A black wood stove and a white refrigerator are positioned nearby. Light wooden walls create a cozy atmosphere.
Cabin in Oxford
4.94 out of 5 average rating, 133 reviews

Thompson Lake, No Cleaning Fee Pine Point Cottage,

BridgetRating, 5 stars1 month ago
wonderful birthday weekend stay. very clean, quiet and peaceful! we had everything we needed to stay busy in the rain! very responsive host
Guest favorite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway
4.95 out of 5 average rating, 157 reviews

The Conscious Cabin

DrewRating, 5 stars5 days ago
Does the cabin look perfect in the photo? It's better. Does the yard look like the perfect place to forget the rest of the world exists? It is. Are the White Mountains a place that make you feel like the psychological mountains in your life are just a little smaller? They are. We don't have enough good things to say about the Cabin or communicating with Cassouki. It's rare to step into a space that feels like it was designed with intention on every level - from the scents in the air to the textures of the cabin to the quiet confidence in every object's placement. The Conscious Cabin doesn't just reflect a designers eye, it reflects a storyteller's heart. I've stayed in more than a few retreats, but this is the first one that felt like it had something to say--and somehow said it quietly enough to let us hear ourselves again. Stay here.
Guest favorite
A contemporary cabin constructed from western red cedar is nestled among trees, featuring a spacious deck with two red chairs. Nearby, a wood-fired cedar hot tub sits on a platform, surrounded by a natural setting marked by fallen leaves and foliage.
Cabin in Appleton
4.93 out of 5 average rating, 316 reviews

Smitten - you will be - Hear Silence.

JustinRating, 5 stars3 weeks ago
such a peaceful, charming place. total privacy and very clean, would definitely stay again
Guest favorite
Cabin in New Vineyard
4.91 out of 5 average rating, 113 reviews

Mill Pond Waterfront Cabin On The Way To Sugarloaf

JeffryRating, 5 stars2 weeks ago
very much worth the money to stay, Farmington is a beautiful town and the cabin is gorgeous with the view onto mill pond.
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, 109 reviews

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

RonniRating, 5 stars8 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.
Guest favorite
Cabin in Parsonsfield
4.96 out of 5 average rating, 225 reviews

Riverfront cabin between Portland & White Mtns.

MarcoRating, 5 stars3 weeks ago
Very cozy cabin, easy for multiple people to stay in. Great atmosphere with inside and outside speakers, a beautiful river, and a great fire pit location. Highly recommend staying here.

Quick stats about vacation rentals with a kayak in Winthrop

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$18,823 GYD 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