Vacation rentals with a kayak in New Fairfield

Find and book unique kayak rentals on Airbnb

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Popular amenities for New Fairfield kayak rentals

House rentals with a kayak

Guest favorite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars3 weeks ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Superhost
A charming house features a distinctive red-roofed turret and light-colored exterior, framed by landscaped green lawns and lavender plants. A tree-lined path leads to the entrance, offering a sense of seclusion and tranquility.
Home in Port Jefferson
4.81 out of 5 average rating, 329 reviews

The Hilltop Harborview

DarrellRating, 5 stars1 week ago
Very quiet and peaceful.
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, 56 reviews

Hudson Valley Glass-sided Lakehouse

SharonRating, 5 stars1 month ago
What a fabulous place. Took me and my husband right back to the 1970s. Gorgeous 270° view of a very beautiful lake. Very peaceful, comfortable with all the amenities needed to relax and enjoy. Master bed was so comfortable. I wanted to buy it. Beautiful plants all over with humongous 16 foot sliding glass doors overlooking the lake. Plenty of interesting books to read and hundreds and hundreds of albums to listen to from the 40s to the 80s. Michael and Ivy were very accommodating with recommendations and we’re available at any time with questions and such. We will absolutely stay there again, considering it actually as a yearly getaway. Great job guys. Thanks for our beautiful stay
Guest favorite
The exterior of a custom-built luxury lake house is shown, featuring natural stone and wood elements. A spacious deck surrounds the upper level, adorned with plants. Below, a patio area has two lounge chairs, while a well-maintained lawn and greenery enhance the setting.
Home in Greenwood Lake
4.97 out of 5 average rating, 186 reviews

The Best Lake House! *Ask About Boat Use Promo*

KevinRating, 5 stars3 weeks ago
This beautiful lake house is a lovely retreat from the chaos of the city. We spent the day lounging by the dock, and relaxing in the sun. It was awesome to have a full private bar with your own pool table right in the house!
Guest favorite
The exterior of a modern house is illuminated by warm lights during twilight. Large windows and multiple balconies showcase the architecture, surrounded by trees and natural greenery. A gravel path leads towards the house, enhancing the inviting ambiance of the mountain setting.
Home in Mount Tremper
4.96 out of 5 average rating, 103 reviews

Chef's kitchen, seclusion, and breathtaking views

ChristopherRating, 5 stars5 days ago
This is a great place to stay. We had eight adult men staying for a healing weekend and everyone had their own room. Location is fantastic, views gorgeous, and the amenities were thoughtfully appointed.
Superhost
A charming house with a sloped roof sits alongside Candlewood Lake. Lush greenery frames the property, while white flowering shrubs add a touch of natural beauty. The serene water reflects a clear blue sky, creating a peaceful lakeside setting.
Home in Danbury
4.67 out of 5 average rating, 18 reviews

Enchanting 3 Bedroom Lake House on Candlewood Lake

RyanRating, 5 stars9 months ago
Yasmina was such a great host! We stayed at the Airbnb for our wedding weekend. The house made the whole weekend a perfect one! Would absolutely recommend! Thank you again for all of your help Yasmina!
Guest favorite
A covered porch features comfortable seating with soft cushions, offering expansive views of the lake and surrounding trees during sunset. The warm light casts a golden hue, enhancing the serene outdoor space, while a small table sits in the center, inviting relaxation.
Home in Pine Plains
4.98 out of 5 average rating, 123 reviews

Twin Island Lake House • Hot Tub

KaiRating, 5 stars2 weeks ago
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.
Top guest favorite
The exterior of the retreat is illuminated at dusk, highlighting its distinctive architecture with large windows and a welcoming porch. The rustic screen house features string lights, creating a warm ambiance against the backdrop of surrounding trees.
Home in Claryville
4.99 out of 5 average rating, 123 reviews

The Blue House on the Hill Catskills

MarcieRating, 5 stars2 weeks ago
Nora’s house stands out as one of the best that I have stayed in. It feels like visiting the home of a relative who has taken care to ensure modern comforts while preserving the character and history of the home. It’s full of antique furniture and special treasures from china plates to vintage games. The views are breathtaking from indoors or out, and the covered deck allows for grilling or lounging even in the rain. One note: the pull-down stairs to the loft are quite steep. We used it as a daytime clubhouse until our kids, ages 9 and 10, got the courage to sleep up there on our last night. We loved hiking along the creek and visiting the farm animals. Bring tall wading boots if you are visiting in cool weather! Although we could see the adorable pigs and goats from the living room, we thankfully couldn’t smell or hear them unless we went down the hill to say hello. Nora was helpful, responsive, and friendly. I am grateful to her for making our stay so special. Highly recommended!

Cottage rentals with a kayak

Superhost
A serene outdoor pool area is surrounded by a wooden deck and natural greenery. Pool floats lie on the water's surface, and a few lounge chairs are arranged nearby. Lush trees and shrubs create a tranquil backdrop, enhancing the connection to nature.
Cottage in Kingston
4.8 out of 5 average rating, 173 reviews

Cottage with Private Deck on 8 acres of Woods

MattRating, 5 stars2 weeks ago
Cozy, quaint, cute space. Perfect for a couple or a single adventurer. Gorgeous location and amenities. Would happily re-book!
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 stars2 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, 35 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

MollyRating, 5 stars2 weeks ago
Was visiting the area from Chicago for a friend’s wedding. The place was in such a cute neighborhood. I loved taking morning walks with our pup to ball pond and enjoying the peacefulness of the surrounding neighborhood (which was quiet and friendly!). Upon arrival it was very clean and well organized. The plus was the fenced backyard so our dog Andee could enjoy relaxing in the grass. There were also a bunch of great restaurants nearby and easy to door dash. Overall really enjoyed the stay and would book again!
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, 102 reviews

Waterfront Joshua Cove Cottage with private beach.

ConnorRating, 5 stars2 weeks ago
Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!
Top guest favorite
The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.
Cottage in Highland Lakes
4.97 out of 5 average rating, 327 reviews

The Mountaintop Lakehouse that Time Forgot.

MaryBethRating, 5 stars2 weeks ago
Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go 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, 268 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 tranquil lakeside area features a private dock with lounge chairs and an umbrella, providing a place to relax by the water. Nearby, a wooden deck leads to the charming cottage, surrounded by lush greenery and trees, creating a serene atmosphere.
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars2 weeks ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!
Guest favorite
A welcoming living area features two comfortable sofas adorned with decorative pillows. A geometric area rug sits beneath a central coffee table. Large sliding doors, framed by white curtains, provide scenic views of the lake and access to the outdoor deck.
Cottage in Ulster Park
4.91 out of 5 average rating, 180 reviews

Romantic House on a Magical Lake

VidhiRating, 5 stars2 months ago
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.

Cabin rentals with a kayak

Guest favorite
An outdoor fire pit surrounded by four wicker chairs is set against the backdrop of a modern black cabin. The gravel area is decorated with native flowers and greenery, offering a cozy spot for gathering. A wooden deck with stairs is visible in the background.
Cabin in Greenwood Lake
4.99 out of 5 average rating, 89 reviews

Modern Nordic Designed Cabin

FeRating, 5 stars6 days ago
The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!
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 stars2 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!
Superhost
An aerial view captures the ECHO cabin nestled among lush greenery, with private access to serene waterfront. The structure is framed by trees, highlighting the expansive lawn leading to the lake's edge, providing a tranquil retreat surrounded by nature.
Cabin in Wantage
4.85 out of 5 average rating, 136 reviews

ECHO cabin - lakefront peaceful modern house

VictoriaRating, 5 stars6 months ago
Very cozy, private, clean and feellikehome spot. Beautiful house on the lake with everything you need. Definitely would stay there again and recommend to everyone who is looking forward for a little getaway from busy life. Great host, responds quickly if any questions, clear instructions and info made my stay super comfortable and memorable. Great experience.
Superhost
Cabin in Kerhonkson
4.93 out of 5 average rating, 164 reviews

Cozy Cabin with Pond on Six Acres

JayvonRating, 5 stars3 months ago
We had an amazing valentines weekend and my dog couldn’t have had more fun ! This private cabin in the neck of the woods can truly be described as a real getaway ! It has a beautiful landscape and is strapped with everything we needed and more. After a full day of hikes in the local area, we found ourselves snowed in and enjoyed some card games. We had an outdoor fire in the stone pit and made some smores. Colleen and Julian were also super accommodating for us due to the weather conditions as well. They are beyond helpful ! Thank you guys ! Will definitely be back !
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, 79 reviews

Cabin by the lake I Private Beach I Paddle Board

EmilyRating, 5 stars5 days ago
I recently stayed at Mariana’s place for a work trip over the weekend. While I sadly did not get to enjoy the home and area much, it was a wonderful spot to relax at the end of the day! The bed was comfortable and the kitchen/bathroom had everything you would need and more. I’d highly recommend staying here if visiting the Litchfield area!
Guest favorite
A rustic red cabin is set against a snowy landscape, framed by tall trees. A wooden deck extends from the front, providing access to the entrance. The surroundings are blanketed in snow, creating a serene winter scene.
Cabin in Colebrook
4.94 out of 5 average rating, 94 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

EdwardRating, 5 stars1 week ago
Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!
Guest favorite
The cabin is illuminated at dusk, situated on a hillside overlooking a gently flowing river. Leafless trees frame the scene, and scattered leaves cover the ground. The water reflects the soft glow from the cabin, creating a serene atmosphere amid nature.
Cabin in Red Hook
4.97 out of 5 average rating, 87 reviews

Secluded luxury: modern riverfront fishing cabin

JamesRating, 5 stars3 weeks ago
Beautiful & peaceful weekend getaway. I highly recommend Samuel & Catherine’s cabin and will be coming back in the near future.
Guest favorite
A wooden deck is shown featuring a large umbrella providing shade over a seating area. A patterned rug lies on the floor, accompanied by a potted plant. Two lounge chairs and a small table create a comfortable outdoor space, surrounded by lush greenery.
Cabin in Saugerties
4.87 out of 5 average rating, 185 reviews

Private Woodstock Getaway w Hot Tub

ErinRating, 5 stars5 days ago
We had a wonderful stay at Marta's house. Everything was spotless, well cared for and thoughtful. The check in process was so simple and the house rules were easy to follow. The record collection was such a nice touch, especially on a rainy Saturday afternoon and the basement with a full media setup and games was perfect for a Saturday night in. The beds were comfortable, plenty of towels and amenities and the hot tub was great as well! The location was also great! Nothing bad to say about this amazing little spot :-)

Quick stats about vacation rentals with a kayak in New Fairfield

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$27,189 GYD before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore