
Vacation rentals with a kayak in New Haven
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House rentals with a kayak

Newly Built Beach House Getaway
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!

The Hilltop Harborview
Very quiet and peaceful.

Bliss by the Sea - Cozy Beachside Escape
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.

Romantic Couples Retreat with Private Sandy Beach
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.

Serenity by Lakefront Cottage!
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

Seaside Home - Walk to Beach & Marina
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!

Hilltop Retreat- Lakefront with Dock
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

Hang by the (Chel)SEA
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

Beachfront Cottage Serene Private Beach, Kayaks
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.

Salty Kisses Beach Cottage Milford CT
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!

Longview Lakehouse - 5 min walk to private beach
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!

Sunset Cabin Modern Home Kayak FirePit Lake Access
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!

Direct Waterfront Cottage on Moodus Reservoir.
Nice little spot with boats on the pond. Went there for my son’s Wesleyan graduation and could take family out on the kayaks.

Cheerful 3 Bedroom Cottage with Fire Place
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.

Charming Fairfield Beach 3BR Cottage By The Sea
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.

Ret's Coastal Cottage w/Private Association beach
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

Lakefront cabin with private dock on stunning cove
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!

Beautiful lakeside summer home
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...

Lakeshore Cabin with boat dock
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!

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

Swim, fish, kayak & RELAX!
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.

Candlewood Cabin - with Private Waterfront
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!

Cabin by the lake I Private Beach I Paddle Board
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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- Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Cooper's Beach, Southampton
- Dunewood
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Thunder Ridge Ski Area
- Bethpage State Park
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- Ocean Beach Park
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- Sunken Meadow State Park
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