Vacation rentals with a kayak in New Haven

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Popular amenities for New Haven kayak rentals

House rentals with a kayak

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.
Superhost
A spacious lawn is surrounded by mature trees, providing shade and greenery. A vintage home is visible, with outdoor seating and a grill setup nearby. Gravel paths lead through the property, inviting exploration of the shared outdoor space.
Home in Rocky Point
4.87 out of 5 average rating, 238 reviews

The Katalpa House -by the beach

KyleRating, 5 stars3 weeks ago
The house was great for my family of five. We stayed there for my daughter's graduation at Stony Brook University, which was about 25 minutes away. All the grocery stores and restaurants were nearby, so there was no need to drive far. The beach is just a short walk from the house, and the kids enjoyed collecting beautiful rocks there. The house had everything we needed, so we did not have to contact John for anything. John was very responsive when I messaged him about my flight delay and even offered to extend our stay by several hours after our checkout time. Overall, we enjoyed this place and had a great time in Long Island.
Guest favorite
A blue kayak rests on a wooden dock overlooking calm waters. Lush greenery surrounds the inlet, with trees reflected in the water. Soft clouds dot the sky, hinting at a serene evening ambiance.
Home in Fairfield Beach
4.9 out of 5 average rating, 21 reviews

Seaside Home - Walk to Beach & Marina

PeterRating, 5 stars3 weeks ago
This was the second time staying at Angela’s place and it was a great experience, again! The location is great and the back yard is so peaceful and cozy. My family says it feels like it’s our Fairfield Home! I would highly recommend it! First Class!
Superhost
Home in Sandy Hook
4.83 out of 5 average rating, 6 reviews

Serenity by Lakefront Cottage!

SabrinaRating, 5 stars3 weeks ago
The amazing place to spend with your partner, all clean, a beautiful view from the balcony, I loved it, I would come back more often
Guest favorite
Two bright red Adirondack chairs are positioned on a grassy area near a serene waterfront. A wooden dock extends into the water, surrounded by lush greenery and trees. A peaceful atmosphere is created by the natural surroundings.
Home in New Fairfield
4.97 out of 5 average rating, 75 reviews

Hilltop Retreat- Lakefront with Dock

JoeRating, 5 stars2 months ago
Our stay included spending family time in front of the fireplace watching Disney shows and with time spent enjoying meals around the cozy kitchen table. Enjoyed our stay very much and hope to go back one day
Guest favorite
A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.
Home in Morris
4.86 out of 5 average rating, 151 reviews

Bantam Lake Waterfront Retreat with Private Beach

AnnetteRating, 5 stars1 month ago
This lovely lakeside cottage was the perfect backdrop for a family weekend away! Thank you to our host for being extremely accommodating and kind!!
Superhost
A calm pond reflects the surrounding greenery, featuring well-maintained grass leading up to the home's deck. A red kayak rests on the lawn, positioned beside the house, inviting aquatic activities. The scene is framed by leafy trees and a clear blue sky.
Home in Meriden
4.75 out of 5 average rating, 85 reviews

Relax by the water in a 4 bedroom house

MadelinRating, 5 stars1 week ago
We had a great time at Tonya’s place visit CT from AZ with the family for nephew’s wedding. Convenient location, spotless and very comfortable it felt like home.
Guest favorite
A cocktail is presented in a tall glass with a vibrant green stem, garnished with red berries. Sunlight glows in the background, reflecting off the water. A white adirondack chair is visible nearby, set against a tranquil evening scene.
Home in Branford
4.95 out of 5 average rating, 19 reviews

Breathtaking Panoramic Waterfront

GlennRating, 5 stars3 days ago
A spacious property in a wonderful location. The house was exactly as advertised. Karen is an excpetionally responsive host. Our family (6 adults, 4 children) felt entirely comfortable there, and the kids especially enjoyed the pool.

Cottage rentals with a kayak

Guest favorite
A charming waterfront cottage is seen from the water, surrounded by lush trees. A spacious deck with a canopy extends outward, while two individuals enjoy the water on a paddleboard. The shoreline features a rocky edge and a grassy area leading up to the cottage.
Cottage in Branford
5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

BasilRating, 5 stars9 months ago
We loved it. Redefines “fully stocked” - David’s place had everything we could ask for. The water at high tide was magical. Kayaking, fishing and we found over 100 (literally) hermit crabs.
Top guest favorite
A two-story cottage features horizontal siding and a distinctive light blue front door. A large window is positioned above the entrance, allowing natural light to enter. The garage is on the ground level, with a small staircase leading to the entryway.
Cottage in Milford
4.92 out of 5 average rating, 51 reviews

Salty Kisses Beach Cottage Milford CT

LisaRating, 5 stars9 months ago
We had a wonderful stay at Salty Kisses. The home is very comfortable and extremely well appointed. We enjoyed the proximity to the ocean as well as the ability to relax in the yard on the hammock or by the fire pit. Denise was very responsive to all communications and gave us lots of information about the area. Thank you for being such a great hostess!
Top guest favorite
Two wooden chairs are positioned on a grassy area overlooking the calm water. A fire pit sits in between the chairs, and a swing hangs from a nearby tree. In the background, a dock extends into the water, framed by trees.
Cottage in Shelter Island
4.97 out of 5 average rating, 108 reviews

Shelter Island Waterfront Getaway

CindyRating, 5 stars5 months ago
Great stay, Maureen is very communicative and super helpful. Beautiful views
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!
Guest favorite
A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.
Cottage in Moodus
4.9 out of 5 average rating, 131 reviews

Direct Waterfront Cottage on Moodus Reservoir.

WendyRating, 5 stars2 weeks ago
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.
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
4.85 out of 5 average rating, 82 reviews

Cheerful 3 Bedroom Cottage with Fire Place

MarciaRating, 5 stars1 month ago
A house on the water in beautiful Milford, CT, this was a great place to stay during Easter break. Clean, well stocked and cozy, I'd recommend this place for a lovely beachfront getaway.
Top guest favorite
A bright sunroom features a round table surrounded by two white metal chairs with blue cushions. Large windows allow natural light to fill the space, showcasing a coastal view. Straw hats are hung on the walls, adding a touch of seaside charm.
Cottage in Fairfield Beach
4.98 out of 5 average rating, 120 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

BriannaRating, 5 stars9 months ago
We enjoyed our stay! Such easy access to the beach was so convenient. You’re definitely better off venturing out after high tide to enjoy the most amount of beach and there are a lot of shells that make being barefoot challenging. We did arrive after major storms which could have contributed to that. The house was spotless with everything you need to be comfortable! We did not utilize the outdoor space but definitely would have if the weather was drier! Definitely would stay here again.
Guest favorite
A serene view of an inlet bay beach is presented, featuring soft sandy shores leading to calm waters. A swan stands gracefully in the water, with the shoreline visible in the background, framed by trees and houses on the opposite side.
Cottage in Short Beach
4.96 out of 5 average rating, 48 reviews

Ret's Coastal Cottage w/Private Association beach

LauraRating, 5 stars2 weeks ago
This cute, comfortable and sun-filled cottage was perfect for our needs, and close to where our son lives, which was great! Everything was just as pictured, super clean, beautiful main bathroom, very well-stocked kitchen, comfortable bed and tons of storage in master bedroom. Living room was spacious and comfortable and everything was nicely decorated. We took advantage of the kayaks, and the backyard grill, and the yard is gorgeous! We walked every morning. Catherine was helpful, responsive and flexible throughout our stay, and we are already making plans to return next year!

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!
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 stars9 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...
Top guest favorite
A spacious outdoor area features a private dock along the lake, with multiple lounge chairs positioned for relaxation. Lush greenery surrounds the well-maintained yard, and a series of steps leads to the cabin. Soft lighting enhances the serene environment at dusk.
Cabin in East Haddam
5 out of 5 average rating, 18 reviews

Lakeshore Cabin with boat dock

IrenaRating, 5 stars3 weeks ago
We spent a long weekend at Dennis’ place and it was nothing short of amazing. Our aim was to relax and enjoy the lake, and we did just that. The house was exactly as described, matched and exceeded our expectations; furnished and the kitchen had everything we needed and more. If we’re back in CT, we won’t hesitate to book the house again! Thanks for being wonderful hosts!
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, 330 reviews

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

JenRating, 5 stars3 days 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 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 stars2 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.
Superhost
A quaint cottage is situated amidst a lush yard, surrounded by trees and colorful foliage. A pathway leads to the front door, while a swing hangs from a nearby tree. Leaves cover the ground, complementing the natural setting.
Cabin in South Salem
5 out of 5 average rating, 4 reviews

Casa Luna Lake Cottage

DanielRating, 5 stars2 months ago
The place was perfect for what we were looking for in a quiet weekend to explore the area. Joann was quick and responsive and went out of her way to make us welcome.
Superhost
Cabin in New Fairfield
4.84 out of 5 average rating, 75 reviews

Candlewood Cabin - with Private Waterfront

CaroleRating, 5 stars3 weeks ago
We really enjoyed our stay. We needed a place near Norwalk and Darien for post-op recovery, and chose this place for the peaceful vibe. I was able to run errands, hike, and even go into the nearby towns to visit Planet Fitness, while my son relaxed and recovered in the cabin. The kitchen had nearly everything we needed for me to cook for a week (there was no skillet, but plenty of pots and pans, knives & cutting boards, utensils—even a pizza cutter). The cabin has a euro-style washer/dryer combo, which has handy if slower than I'm used to. There's a helpful note that says washing/drying takes 6 hours so plan ahead, but I googled the unit and found some handy workarounds. The cabin wasn't supplied with coffee, laundry detergent, dishwashing detergent, or extra garbage bags. Those were easy enough for me to grab when I went grocery shopping, and Scott was very responsive when I let him know. Overall this was a really great experience!
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 stars3 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!

Quick stats about vacation rentals with a kayak in New Haven

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    980 reviews

  • Family-friendly rentals

    10 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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