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

Lake house retreat Granby CT
We were in the area to meet our son's fiance's extended family. Nathania's home was perfect! We had 7 adults and 5 little boys ages 9, 7, 5, 2, and 2 months. There was plenty of space to spread out and enjoy the time together. The hot tub, kayaks, and foosball table were especially popular! We were able to host a family dinner with guests which was wonderful. Everything we needed for preparation was readily available. Lots of beautiful parks, playgrounds, hiking areas. Plenty to keep everyone entertained! Nathania was extremely kind, gracious, and responsive to questions. We had absolutely zero issues. So grateful for a wonderful vacation. Thank you for sharing your idyllic home with us. We hope to visit again!!!

Creekside Cottage
Jenai's place was cozy and comfortable, with all the amenities you could hope for. We enjoyed cooking in the beautifully remodeled kitchen, soaking in the big tub, and relaxing with charming water views.

Water's Edge Lakefront Home
WOW!! We cannot say enough amazing things about our stay. We stayed for the holidays and the snow surrounding the lake was the most beautiful surrounding imaginable. It was so peaceful and we watched both sunrises and sunsets there. Plus there were tons of beautiful swans to appreciate! The house was extremely pristine, decorated beautifully for the holidays, and felt like home. This was such a special stay and our host was so accommodating! We will absolutely be back.

🛶 Lakefront Paradise with Your Own Private Beach🏖
Everything was perfect ! My family and I had a great time. Looking forward to staying here again in the summer.

Twin Island Lake House • Hot Tub
Anne Marie's place was exactly what we were looking for! It is extremely well stocked, with everything you might need, from kitchen appliances, extra blankets, many towels, etc. The surroundings were gorgeous and the area is very quiet and peaceful. Anne Marie was friendly and very responsive, answering questions quickly and flexibly. We can't wait to come back!

Creekside Retro Escape
This place was amazing. My team and I stayed here for a race weekend, and everyone loved it. There were lots of cool birds that were in the river nearby or the backyard, which made for some fun bird watching. I highly recommend!

Aster Place
Beautiful home! My boyfriend and I had a great time. It’s super clean and the beds were so cozy. Would definitely go back :)

Peaceful Riverfront Cottage with Private Hot tub
We had a wonderful weekend getaway. The place was spotless and neat. Adele was very responsive and communicated very clearly. The location was quiet, safe, and peaceful. It was close to towns with lots of cafes, restaurants, bars and shops. Highly recommended!
Cottage rentals with a kayak

Private Lake House 1 Hour to NYC & Near Westpoint
Stayed here with some friends for my birthday and it was wonderful. Ben is very friendly, responsive and made sure to take care of us. The views of the backyard were beautiful and peaceful. We also had lots of privacy. Will definitely be booking again in the future!

Cottage with Private Deck on 8 acres of Woods
The perfect place for a cozy getaway from the city! We really needed an R&R and this place gave us what we needed and would be happy to come back here again ✨

Be in Nature at this Gorgeous Riverfront Cabin
Mark was a responsive host who was very flexible and considerate of our needs (family of 4 with 2 kids) with early check in. His house is beautifully decorated and organized for a comfortable stay with breathtaking views of the surrounding landscapes . Most of all my kids enjoyed just running around the grass and being in nature, core memories , you can’t put a price on. Hopefully we will see you again.

The Cottage at Indian Cove
I thoroughly enjoyed my stay at this peaceful cottage. I enjoyed sipping my coffee looking at the view of the cove from the deck and the bird watching from the screen porch was a delight. The bed was comfortable and Gail stocked the kitchen with drinks and snacks! Gail's house is next door but the layout of the deck and screen porch offers great privacy. A perfect place to get away from it all and relax in nature.

Cozy Getaway | Pet Friendly | Litchfield Cty
Such a cozy space!!! My small family really did enjoy our peaceful stay. I would definitely book again when in the area. I felt such peace and serenity sitting under the stars, in front of the crackling campfire. It was me and the hubby with 2 of our girls ages 10 and 16. They loved the hot tub and s’mores:). Thanks for the stay.

Romantic House on a Magical Lake
Comfortable and clean with beautiful scenery - on clear days, you get a Mountain view across the lake! Highly recommend.

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.

Lakefront Cottage near Hudson Valley
Stayed for a long weekend with my wife and two dogs. Cottage was comfortable and clean with an amazing view of the lake with a nice patio and access to the dock which we enjoyed. Also great location just a bit over an hour from the city but within a 15 minute drive to many great hikes and close to many great food options. Tony was also very responsive and helpful with recommendarions. Highly recommend.
Cabin rentals with a kayak

Modern Nordic Designed Cabin
We had a great stay at this cabin! The location was on a dead end street which made it very quiet, serene, and private. The lake was visible from the back porch of the house & a very close walk away. The house comes with access to a semi-private beach/dock area which is the perfect place to spend the day in the summer. The house was decorated beautifully while being extremely comfortable at the same time. Our host, Kamil, was very responsive. If I had a question or concern he was extremely helpful within a short period of time. All around, really enjoyed this stay & would definitely return when in this area again!

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit
This place was so peaceful and gorgeous! We stayed here during the A Weekend in the Life event and it was such an easy drive into town and to all the activities. The house itself had great amenities and things to do! During our stay, the heater did break, but our host was on top of it. The house has a pellet stove that kept it toasty, so she had 5 bags of pellets delivered to the house for us, she had someone come out and service the pellet stove and she had someone come out to service the heat all in one day! They were accommodating and helpful. We also had our dogs with us who has plenty of space and the airbnb didn’t smell like dog. You couldn’t tell it was a pet friendly place. We loved it!

Swim, fish, kayak & RELAX!
Carrie was very attentive and concerned about giving me the best instructions to make me feel at home. I didn't struggle to check-in and get settled. What ever question or concern I had she would answer me quickly and kindly. I recommend this beautiful place that will make you feel welcome and at home. Thank you for being an amazing host and being extremely caring, and sweet.

Cozy Cabin with Pond on Six Acres
We had an amazing valentines weekend and my dog couldn’t have had more fun ! This private cabin in the neck of the woods can truly be described as a real getaway ! It has a beautiful landscape and is strapped with everything we needed and more. After a full day of hikes in the local area, we found ourselves snowed in and enjoyed some card games. We had an outdoor fire in the stone pit and made some smores. Colleen and Julian were also super accommodating for us due to the weather conditions as well. They are beyond helpful ! Thank you guys ! Will definitely be back !

Cozy Cabin w/ Fireplace | On Lake
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!

Secluded luxury: modern riverfront fishing cabin
We booked this trip last minute during our daughter’s spring break. It was a little under 2 hours from NYC and felt like a world away. The hosts were always available and helpful with everything down to local suggestions. Every detail of the cabin is thoughtfully laid out and provided. We slept four comfortably, but mostly spent our time outside. The property alone offers many trails to explore and made us feel entirely off the grid. The porch around the cabin had locks which would be great for young kids or pets. The surrounding towns were cute and restaurants were excellent. Everything including a supermarket seems to be 10 minutes or under, but we mainly liked staying on the property. We can’t wait to come back in warmer months to go tubing!

Private Woodstock Getaway w Hot Tub
Beautiful house! We enjoyed our stay and found the house to be very comfortable and cozy! The location was great and felt very secluded but yet still very close to town. Loved all the amenities the house had to offer and the dogs enjoyed playing in the yard. The art and records in the house were a great touch. We would love to come back again!

West Hill Cabin
This fishing weekend is a tradition that spans 50 year. We had three generations there this weekend to enjoy the cabin and the fishing derby. The home was beautiful we all had a memorable weekend. Could have done without the snow but that in New England weather for you. And the owner was super easy to work with.
Quick stats about vacation rentals with a kayak in New Fairfield
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ477 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Yale University
- Yankee Stadium
- Inwood Hill Park
- Bronx Zoo
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Woodmont Beach
- Rye Town Beach
- Walnut Public Beach
- Seaside Beach
- Jennings Beach
- TPC River Highlands
- Taconic State Park
- Thunder Ridge Ski Area
- Bethpage State Park
- Marvin Beach
- Sunken Meadow State Park
- Ringwood State Park
- Rockland Lake State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Tamarack Country Club
- Stehli Beach
- The Ridgewood Country Club