
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 Getaway: Beautiful Waterfront - New Milford CT
Absolutely Magical Stay! I can’t say enough good things about this place! From the moment we arrived, we were blown away by the peaceful atmosphere and stunning views. The highlight, hands down, was the serene lake right in the backyard—waking up to the sound of birds and sipping coffee with that view felt like a dream. We especially loved the complimentary kayaks! Paddling around the lake during sunset was pure magic—calm waters, golden skies, and total tranquility. It felt like our own private retreat away from the world. The home itself was spotless, beautifully decorated, and super cozy. The hosts were incredibly thoughtful and responsive, making sure we had everything we needed. Whether you’re looking for a romantic escape, a relaxing solo getaway, or a fun adventure with friends, this place is a hidden gem. We’ll definitely be back!

Beach House in Private Community on LI Sound
Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.

Stay at Old Dorset Farm & create lifelong memories
It is simply a charming place that is saturated with love, respect and care! We loved staying there; its quiet comfort, warmth, tasteful atmosphere. It felt like we weren’t renting a house but were being guests and the host just stepped out for a second and will be right back. Ninka was very kind and accommodating to us; a great communicator; and extremely helpful. We are looking forward to coming back to the warmth and comfort of her house very soon!

Waterfront with private dock & bocce court
We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

Beachfront paradise- come, stay, relax!
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!

Lux cozy 2br/1ba Milford bungalow-walk to beach!
Beautiful home Amazing amenities and extremely clean. Will be renting again as my daughter is at college close by! So nice to know we can come and stay somewhere that feels like home …

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens
This house was very good for me and my friends and we would love to go back!

Coastal getaway with water views in every room
Meaghan’s place was everything we needed and more! Loved the views, the waves, the sea breeze, the bird observing, the walks to Grass Island, the together time with family in a quiet, secure & well appointed setting. Meaghan equipped us with everything! She was very responsive to answer questions. This is one of those treasured memories. Can’t wait until we get back again to this special location! Thank you!
Cottage rentals with a kayak

Waterfront Joshua Cove Cottage with private beach.
We spent Thanksgiving in the beautiful Joshua cottage. This was one of the best Airb&b stays we have ever had. The hosts were wonderful- making sure we had everything we needed. The spot directly on the water is magical.

Salty Kisses Cottage Relax
Our stay was perfect! The home was so clean and Denise even left us a baby gate for our 1 year old. Denise was very responsive and provided great recommendations of places to eat and things to do. There is a private beach across the street but we walked about .25 miles down the street to the Silver Sands State Park beach so that our 1 year old could play in more shallow water before high tide. We would highly recommend and will be back!

Caroline Beach Escape
Wonderful beach cottage. Exactly what we had expected with great charm and beautiful view. The beach cabana was definitely the best part. Suzanne was a wonderful host- very responsive and helpful!

Cottage at the Marina
My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.

Your own Thimble Islands private cottage!
Everything about this stay was as near too perfect as possible. First Sean was proactive, quickly responded to any questions and his pre-visit communications were comprehensive. The pictures accurately describe the house but in reality, they do not do it justice. There are water views from every window. The place and views are amazing!! It is just what we were looking for, on the ocean, private and peaceful. Short drive to the village with shops and restaurants. Highly recommend for a couple who is looking for an escape, you will not be disappointed

SanctuaryCottageByTheSea-Kids, Pets, Waterfront
What an incredible experience! Was a bit hesitant after reading pets were allowed as one of our friends is allergic to dogs and cats - the cottage was super clean and no sign that a “furbaby” had ever been there. Had a personalized welcome letter for our party of 6, and favorite beverages thanks to advance questions and special touches from Mickey. Loved listening to the waves, reading by the fire and getting in a game of ping pong at the outdoor table. Every detail has been considered from the 3 charging stations to the guidebook and more. There are positive quotes and signs in the cottage and we were so relaxed and recharged. Will definitely book again. 5 stars all around! Thank you.

Shore home in private community, away from it all
Gwyn was an exceptional host and the cottage was absolutely perfect as a peaceful getaway. We would love to visit again when looking to get away from the hustle and bustle of the day to day!

Ret's Coastal Cottage w/Private Association beach
Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again
Quick stats about vacation rentals with a kayak in New Haven
Total rentals
20 properties
Nightly prices starting at
$50 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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