Vacation rentals with a kayak in Fairfield County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Fairfield County kayak rentals

House rentals with a kayak

Superhost
A view of the tranquil water features small boats gently bobbing in the distance. Nearby, a sandy beach meets the shoreline, with houses lining the coast under clear blue skies.
Home in Milford
4.92 out of 5 average rating, 25 reviews

Beachfront getaway in Milford

AllisonRating, 5 stars10 months ago
My husband and I stayed here with my mom, 3 yr old, and infant and had a lovely time. The house had everything we needed and nothing we didn’t need. This place was no frills but right on the water, and the price reflects that. Stairs are a bit on the steeper side so just be aware of that if you have anyone with bad knees or children learning to use stairs still. Our host was wonderful and very responsive, we liked him a lot! The beach out front is a bit rocky, so water shoes are a must. But it is so beautiful and peaceful! Our favorite thing was going out during low tide with the kids, you can walk really far out and we saw lots of horseshoe crabs and it was so much fun.
Guest favorite
A natural stone patio is surrounded by lush greenery, featuring a round glass table accompanied by four black wire chairs. A fire pit is positioned nearby, and a serene view of the lake is visible through the trees.
Home in Putnam Valley
4.95 out of 5 average rating, 59 reviews

Hudson Valley Glass-sided Lakehouse

Xuan MaiRating, 5 stars3 days ago
Michael's place was exactly what we needed - beautiful, tranquil and quiet. The lake was great to sit next to and look at. The weather was a little cold so not conducive to swimming but I would have definitely gone for a swim if it were warmer. Instead, we spent a lazy afternoon playing records and reading. The grill was convenient (and clean) - we grilled our dinners both nights. And, of course, there was a cute bunny hopping around in the front without a care in the world!
Superhost
A spacious deck extends toward the water, featuring a railing that offers unobstructed views. The surface is light-colored, and the ocean sparkles in the background. The sandy beach is visible to the left, providing a serene setting for relaxation.
Home in East Haven
4.96 out of 5 average rating, 100 reviews

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars6 months ago
This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!
Guest favorite
The three-story house features a light grey exterior with multiple balconies on the front. A double garage is located on the ground floor, with large windows above offering a view of the spacious balconies. The welcoming entrance is framed by well-maintained landscaping.
Home in Milford
5 out of 5 average rating, 8 reviews

New build! 1 house from beach

MartinRating, 5 stars4 weeks ago
Immaculate, beautiful comfortable home on beach block with beautiful water views. Adriana and Robert were amazing, gracious hosts and couldn’t have been more responsive. Among our best Airbnb rentals ever!
Top guest favorite
Home in New Fairfield
5 out of 5 average rating, 33 reviews

Direct Lake Access - Priv Dock, Kayaks, EV Charger

BrentRating, 5 stars3 weeks ago
We had a great stay at the property. It is on a charming location of the lake across the channel from a small wooded island. The home's common spaces were great for gathering and the sleeping arrangements were very comfortable. I would recommend this to any group who wants a lake side experience with a comfortable house.
Guest favorite
A tranquil view of a private beach stretches along the coastline, where gentle waves lap against the smooth sand. Soft clouds dot the blue sky, while beach houses stand in the background, providing a serene coastal ambiance.
Home in East Haven
4.95 out of 5 average rating, 40 reviews

Direct Beachfront Modern Cottage on Private Beach

MacKenzieRating, 5 stars3 weeks ago
We had a great stay at the Airbnb. One thing I haven’t seen mentioned in the reviews or descriptions is that this beach had tons of sea glass! In our short stay we found over 100 pieces and my 4 year old was absolutely delighted scouring the beach for it. There are also tide pools less than a five minute walk from the house. These two things made the stay quite magical for my kids. Otherwise the location is great and the house was very clean. I appreciated the bed on the first level having a trundle as well as a door at the top of the stairs for safety. The house is minimally decorated which is honestly a plus when you don’t have to worry about your kid breaking nicknacks on coffee tables. A few nice throw blankets and nicer glassware would have added to the stay though. Overall we were very happy with this property.
Guest favorite
A scenic view of a beach is captured, featuring gentle waves and a distant island. The adjacent image displays a cozy living area with a sectional sofa, a coffee table on a bright yellow rug, and large windows. The exterior of the raised beach house showcases a balcony and inviting façade.
Home in Milford
4.91 out of 5 average rating, 56 reviews

Cute 2 bed 1 bath beach house

MindyRating, 5 stars9 months ago
The beach house was a great place to be with our family. My boys loved going across the street to the beach. It was walkable to so many places, and short drive. Cozy space and awesome porch deck. Highly recommend staying here.
Guest favorite
Two watercraft are stationed by a lakeside deck: a stand-up paddleboard with a teal design and an orange kayak. The calm lake reflects the surrounding greenery and blue sky, while a wooden staircase leads up to a building featuring large glass windows.
Home in Putnam Valley
4.97 out of 5 average rating, 66 reviews

Waterfront Lake House

KayleeRating, 5 stars1 week ago
Absolutely beautiful stay, Brian is an amazing host and went above and beyond with instructions and helped whenever needed. Their place is located in such a beautiful area, it is quiet and within 10 min drive to stores. The space is very clean and organized. My guests and I felt right at home.

Cottage rentals with a kayak

Superhost
A cottage with a rustic wooden exterior is nestled among trees in a lush green setting. A stone chimney rises from the roof, and a small set of steps leads to the entrance. Surrounding flora includes well-maintained shrubs and mulch, creating an inviting pathway.
Cottage in Cold Spring
4.96 out of 5 average rating, 23 reviews

Romantic Private Lake Art-Deco Cabin Hudson Valley

JamesRating, 5 stars11 months ago
The area was absolutely beautiful. Valhalla Lake was private with stunning views. The cabin was exactly as it was described and the book of directions that was left for guidance was easy to follow.
Guest favorite
A vibrant sunset reflects off the water, casting golden hues across the sky. The landscape features rolling hills in the background and a serene lake bordered by trees and homes along the water's edge.
Cottage in Brookfield
4.92 out of 5 average rating, 36 reviews

Longview Lakehouse - 5 min walk to private beach

MarcRating, 5 stars3 weeks ago
Our stay was fantastic. Traveling with two toddlers, we're always looking for ways to keep them entertained, and there was a plethora of puzzles, games, and toys at the house. The house itself is well maintained and spacious. The community is wonderful with a sandy beach and waterfront playground. The golf cart was an added bonus!
Guest favorite
A bright living room features large windows displaying a colorful sunset. A plush sectional sofa, dressed with several cushions, surrounds a round coffee table. A textured area rug adds warmth to the space, enhancing the inviting and comfortable atmosphere.
Cottage in New Fairfield
4.97 out of 5 average rating, 36 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

AlendaRating, 5 stars2 weeks ago
Great place that looked just like the pictures! We would definitely rent again. Brad always responded right away to my messages.
Top guest favorite
An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.
Cottage in Guilford
4.99 out of 5 average rating, 103 reviews

Waterfront Joshua Cove Cottage with private beach.

KitRating, 5 stars3 days ago
A truly lovely spot! Quiet, relaxing and comfortable. We enjoyed the view of the water, reading on the patio in the lounge chairs and sitting on the bench overlooking the beach. We would love to come back again.
Top guest favorite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 269 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars1 week ago
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!
Superhost
A spacious deck offers a panoramic view of the beach and water, with sunlight reflecting off the surface. Colorful chairs are positioned for relaxation, while shadows created by the railing add depth to the scene. The sandy shore can be seen in the distance.
Cottage in Milford
4.86 out of 5 average rating, 83 reviews

Cheerful 3 Bedroom Cottage with Fire Place

JessicaRating, 5 stars5 days ago
We had a great stay at Jonathan's cottage. The location could not be beat - right on the beach. Jonathan was very easy to communicate with and quick to respond. There were a couple of minor hiccups that occurred but Jonathan was quick and responsive. Overall, a beautiful home in a great location.
Guest favorite
A serene wooded area is shown, featuring tall trees with lush green leaves. Sunlight filters through the foliage, casting gentle shadows on the forest floor. A glimpse of Candlewood Lake is visible in the background, enhancing the natural beauty of the surroundings.
Cottage in New Milford
4.97 out of 5 average rating, 69 reviews

Waterfront, Wooded Cottage on Candlewood Lake

SofiaRating, 5 stars7 months ago
This spot was absolutely wonderful. The lake was wonderful, fireplace was a perfect touch proximity to the elephants trunk flea market was a dream and don and Roz were a pleasure to work with. Local pizza from a menu in the cabin was perfect. I could write a novel on how much we loved this place. Definitely coming back. It was a pleasure :)
Guest favorite
The exterior of a classic cottage is surrounded by trees with colorful autumn leaves on the ground. A stone pathway leads to the entrance, and flower boxes adorn the windows. The lake is visible in the background, providing a scenic view.
Cottage in Newburgh
4.97 out of 5 average rating, 61 reviews

Lakefront Getaway 1 Hr from NYC

Zeke & KrisRating, 5 stars4 weeks ago
I stayed for a month solo to focus on my projects & it was the most peaceful month. The house is contained in nature with a plethora of birds & animal life that I witnessed.. a crane fishing at the creek beside the house as I worked, a pair of woodpeckers hunting at the lawn, a chipmunk that lives under the house & has a morning ritual of its own. All while the lake boasted breathtaking sunsets. On the practical side, the kitchen was fully equipped with everything one needs to cook everyday, which I did. It was private & safe for a solo girl like me to stay a month. Amazon found its way to it no problem. And there are nice streets to take long walks which I did 1 hour a day. Very friendly neighbors, everyone waves at ya. The covered patio, working from the dinner table, waking up in the bedroom to the lake.. all main areas are flanked by beauty. Really was perfect for a solo getaway. Also wifi was very reliable. Keep in mind lake living = insects. They’re harmless. Highly rec renting!

Cabin rentals with a kayak

Top guest favorite
A spacious wooden dock extends over calm lake waters, with a bright yellow kayak and paddles resting on its surface. Lush green hills are visible in the background, reflecting the serene environment.
Cabin in New Milford
5 out of 5 average rating, 8 reviews

Lakefront cabin with private dock on stunning cove

AlekseyRating, 5 stars9 months ago
We stayed here for 7 days with 2 small kids (2 and 4 years old) and wow was it amazing. The home is spacious and has everything we needed inside and outside the house. I could not have asked for anything else from the home and the dock was just so awesome to have, even caught 10+ fish right off the side. We rented a boat for a day from a marina and were able to come in and out of the backyard/house with no problems. I wish we could stay here for a whole month, but have to go back to real life!
Guest favorite
A solitary kayak gently glides across the calm waters of a lake surrounded by lush green hills and scattered islands. The serene sky features soft, fluffy clouds, reflecting a tranquil atmosphere perfect for a day of outdoor exploration.
Cabin in New Fairfield
4.96 out of 5 average rating, 331 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

JenRating, 5 stars1 week ago
We had an absolutely wonderful stay at Jordyn and Gabby’s place! As a full-time patient care provider and with my boyfriend’s demanding job, we were in desperate need of a peaceful and cozy retreat, and this place fit perfectly. The late-night movie setup was a perfect way unwind, the fire pit, soaking in jacuzzi under the moon- all led to this healing trip to be successful! One of the highlights of our trip was kayaking in the nearby waters—it was such a serene experience! We couldn’t have asked for a more personal and relaxing getaway. Our service dog, Loha, also felt right at home and enjoyed every moment of our stay. Thank you, Jordyn and Gabby, for creating such a beautiful space that truly allows guests to recharge and reconnect!
Guest favorite
A serene lakeside scene features a wooden dock extending into the calm water, surrounded by lush greenery. A green canoe rests on the grassy bank, inviting peaceful moments by the lake. The clear blue sky enhances the tranquil atmosphere.
Cabin in Marlboro Township
5 out of 5 average rating, 11 reviews

Cascade-Cabin

SafdarRating, 5 stars3 weeks ago
Our stay was perfect— we were in the area for our son’s college graduation. This place is a hidden gem. It is everything and more. The scenery is unbeatable. Careful attention has been paid to every detail. Steven is the perfect host—he is courteous and was always available. Highly recommend!
Guest favorite
A charming yellow cottage is framed by green trees and a bright blue sky. The exterior features a spacious front porch with large windows and white railings, inviting natural light. Steps lead to the entrance, surrounded by well-kept grass and a few decorative plants.
Cabin in Bethlehem
4.9 out of 5 average rating, 30 reviews

Swim, fish, kayak & RELAX!

GeraldRating, 5 stars3 weeks ago
We stayed for a graduation near by, it was perfect for we were looking for. I wish the weather would have been a bit warmer to enjoy the water.
Top guest favorite
The cabin is surrounded by lush greenery, with warm lights strung across the deck creating a cozy ambiance. Large windows reflect the evening glow, showcasing a welcoming entrance. The sky transitions from deep blue to vibrant orange, adding to the serene setting of the retreat.
Cabin in Bethlehem
4.95 out of 5 average rating, 82 reviews

Cabin by the lake I Private Beach I Paddle Board

AmyRating, 5 stars2 days ago
We loved our stay at Mariana’s cozy and comfortable cabin by the lake. The surroundings are beautiful, and the cabin is tastefully decorated and equipped with everything guests might need. Mariana was quick to respond to our questions, and made us feel very welcomed. The only disappointment was that it rained during our whole stay and we couldn’t enjoy the adorable deck off the side of the house - next time! We’re definitely happy we stayed here!
Guest favorite
Cabin in Harwinton
4.85 out of 5 average rating, 13 reviews

Waterfront Cabin: Love Lake Life

JadeRating, 5 stars1 week ago
I would recommend this stay to anyone who needs getaway escape right on the lake as pictured!! It was a great family bonding trip We enjoyed it all Very close (10 min drive) to Torrington for groceries restaurants or any necessities or activities outside of cabin
The peaceful lakeside view features a wooden dock extending into the calm water, surrounded by rocky terrain and trees. A canoe rests on the shore, while the log cabin's deck is visible in the background, offering a serene outdoor space for relaxation.
Cabin in Holmes

Log Cabin On A Lake With Private Dock

JanaRating, 5 stars2 days ago
Had a great stay at Dutchess Lake. Jason was very communicative and the cabin had everything we needed to make for a relaxing weekend. Would recommend!
The exterior of a stone cottage is surrounded by lush greenery, with a prominent stone chimney rising from the roof. A gravel pathway leads up to the entrance, framed by shrubs and small trees. The setting offers a natural feel, nestled among the trees.
Cabin in Stratford
4.81 out of 5 average rating, 44 reviews

Beautiful lakeside summer home

SondraRating, 5 stars10 months ago
We had a lovely 5-day stay at the cabin on the lake! It was just what we needed. When the weather was nice, we hung out on the dock - there was a hammock to relax in, chairs in the shed, boats to explore with (I went out in a kayak a few times). Lake was peaceful and pretty. The cabin itself was quirky and nice. Yes, hot inside during the days, but with the fully surrounding screened in porch, there was no need to stay inside! Even when it rained, we could be "outside" without being in the elements. The kitchen was well stocked, coffee at the ready, there were plenty of towels and sheets and bed (though we only needed one!), shampoo/ conditioner in the shower, wood ready for the fireplace, board games and more. Honestly, it had everything you'd want for a little getaway. The spot felt secluded while only 5 minutes away from a supermarket. [Okay, you could hear Rte 8 traffic a bit, but it served as calming white noise!] I'd definitely return again...

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