Vacation rentals with a kayak in New Haven

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Popular amenities for New Haven kayak rentals

House rentals with a kayak

Guest favorite
The exterior of a newly constructed home features a combination of blue and white siding. Large windows are present on multiple levels, allowing for ample natural light. A staircase leads to the entrance, while parking is available beneath the house.
Home in Milford
4.84 out of 5 average rating, 57 reviews

Newly Built Beach House Getaway

CaitlinRating, 5 stars3 weeks ago
My husband and I had a family filled weekend for our wedding followed by a mini-moon. We enjoyed every minute of it and we will definitely be booking 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 stars6 days ago
Very quiet and peaceful.
Guest favorite
A charming exterior of a single-story house is presented with light gray siding and a striking teal door. Surrounding landscaping includes vibrant blue hydrangeas and a gravel driveway, leading to a serene view of the nearby grassy area and trees in the distance.
Home in Clinton
5 out of 5 average rating, 7 reviews

Bliss by the Sea - Cozy Beachside Escape

VictoriaRating, 5 stars2 weeks ago
We would stay again. The cottage is well maintained. It was nice to have some basic cleaning supplies so you can touch up if needed. Toiletries, laundry supplies, coffee pods, nice touches, felt like home.
Guest favorite
The exterior of the cottage features a light grey facade with large glass doors opening onto a wooden deck. Lush green grass surrounds the home, accentuated by several trees showing vibrant autumn leaves. A small dining area with white furniture is visible on the patio.
Home in Old Saybrook
5 out of 5 average rating, 39 reviews

Romantic Couples Retreat with Private Sandy Beach

MegRating, 5 stars1 week ago
This is a beautiful private spot. It was so peaceful and quiet. The cottage was very clean, bright with a very soothing color scheme. Lauren was very responsive to any questions we had.
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
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!
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 sandy outdoor area features four blue adirondack chairs arranged in front of a beach house with large glass doors. A blue and white striped umbrella is set up nearby, providing shade, while a small potted plant adds a touch of greenery to the scene.
Home in North Fork
5 out of 5 average rating, 16 reviews

Hang by the (Chel)SEA

JillRating, 5 stars1 week ago
Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.

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!
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 stars1 week 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!
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 stars1 week 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 stars2 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 stars1 day 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 stars1 week 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
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, 78 reviews

Cabin by the lake I Private Beach I Paddle Board

OliviaRating, 5 stars1 month ago
A few of us stayed at Mariana's for a girl's weekend to go to local events- and had a wonderful stay! The apartment was really aesthetic and perfect for a girl's trip, and we loved cooking in the kitchen as she had every appliance we needed, and loved the fireplace. Everything was cozy, well described, and had everything we could have needed! Mariana was friendly and helpful leading up to and during our stay. We'd recommend this for anyone wanting a cozy getaway!

Quick stats about vacation rentals with a kayak in New Haven

  • Total rentals

    20 properties

  • Nightly prices starting at

    G$10,491 GYD 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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