
Vacation rentals with a kayak in New Haven
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Top-rated kayak rentals in New Haven
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House rentals with a kayak

The Hilltop Harborview
Very quiet and peaceful.

The Katalpa House -by the beach
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.

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!

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

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

Bantam Lake Waterfront Retreat with Private Beach
This lovely lakeside cottage was the perfect backdrop for a family weekend away! Thank you to our host for being extremely accommodating and kind!!

Relax by the water in a 4 bedroom house
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.

Breathtaking Panoramic Waterfront
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

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!

Shelter Island Waterfront Getaway
Great stay, Maureen is very communicative and super helpful. Beautiful views

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.

Casa Luna Lake Cottage
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.

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
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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- Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Cooper's Beach, Southampton
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Dunewood
- Bethpage State Park
- Ocean Beach Park
- Thunder Ridge Ski Area
- Woodmont Beach
- Amagansett Beach
- Rye Town Beach
- Seaside Beach
- Quotonset Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Heckscher State Park
- Silver Sands Beach