
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

Once a Pond - time and stress slow down.
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.

The Hilltop Harborview
Very quiet and peaceful.

Hudson Valley Glass-sided Lakehouse
What a fabulous place. Took me and my husband right back to the 1970s. Gorgeous 270° view of a very beautiful lake. Very peaceful, comfortable with all the amenities needed to relax and enjoy. Master bed was so comfortable. I wanted to buy it. Beautiful plants all over with humongous 16 foot sliding glass doors overlooking the lake. Plenty of interesting books to read and hundreds and hundreds of albums to listen to from the 40s to the 80s. Michael and Ivy were very accommodating with recommendations and we’re available at any time with questions and such. We will absolutely stay there again, considering it actually as a yearly getaway. Great job guys. Thanks for our beautiful stay

The Best Lake House! *Ask About Boat Use Promo*
This beautiful lake house is a lovely retreat from the chaos of the city. We spent the day lounging by the dock, and relaxing in the sun. It was awesome to have a full private bar with your own pool table right in the house!

Chef's kitchen, seclusion, and breathtaking views
This is a great place to stay. We had eight adult men staying for a healing weekend and everyone had their own room. Location is fantastic, views gorgeous, and the amenities were thoughtfully appointed.

Enchanting 3 Bedroom Lake House on Candlewood Lake
Yasmina was such a great host! We stayed at the Airbnb for our wedding weekend. The house made the whole weekend a perfect one! Would absolutely recommend! Thank you again for all of your help Yasmina!

Twin Island Lake House • Hot Tub
We had a wonderful stay at this location during my daughter’s graduation from Bard College. The location has beautiful views of the lake and the layout of the property was perfect for the family to gather and celebrate, while also giving everyone the space for their own quiet time or rest. I would definitely recommend this location and hope to have the opportunity to stay again.

The Blue House on the Hill Catskills
Nora’s house stands out as one of the best that I have stayed in. It feels like visiting the home of a relative who has taken care to ensure modern comforts while preserving the character and history of the home. It’s full of antique furniture and special treasures from china plates to vintage games. The views are breathtaking from indoors or out, and the covered deck allows for grilling or lounging even in the rain. One note: the pull-down stairs to the loft are quite steep. We used it as a daytime clubhouse until our kids, ages 9 and 10, got the courage to sleep up there on our last night. We loved hiking along the creek and visiting the farm animals. Bring tall wading boots if you are visiting in cool weather! Although we could see the adorable pigs and goats from the living room, we thankfully couldn’t smell or hear them unless we went down the hill to say hello. Nora was helpful, responsive, and friendly. I am grateful to her for making our stay so special. Highly recommended!
Cottage rentals with a kayak

Cottage with Private Deck on 8 acres of Woods
Cozy, quaint, cute space. Perfect for a couple or a single adventurer. Gorgeous location and amenities. Would happily re-book!

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!

Waterfront Joshua Cove Cottage with private beach.
Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!

The Mountaintop Lakehouse that Time Forgot.
Peaceful surroundings, beautiful lake, wonderful house and amazing hosts! Had an absolute ball kayaking, fishing, and enjoying nature. This was my second trip and can’t wait to go back again.

The Cottage at Indian Cove
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

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.
Cabin rentals with a kayak

Modern Nordic Designed Cabin
The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!

Cascade-Cabin
Our stay was perfect— we were in the area for our son’s college graduation. This place is a hidden gem. It is everything and more. The scenery is unbeatable. Careful attention has been paid to every detail. Steven is the perfect host—he is courteous and was always available. Highly recommend!

ECHO cabin - lakefront peaceful modern house
Very cozy, private, clean and feellikehome spot. Beautiful house on the lake with everything you need. Definitely would stay there again and recommend to everyone who is looking forward for a little getaway from busy life. Great host, responds quickly if any questions, clear instructions and info made my stay super comfortable and memorable. Great experience.

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 !

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!

Rustic Cabin+ Private Beach Pond, Stars & Wildlife
Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!

Secluded luxury: modern riverfront fishing cabin
Beautiful & peaceful weekend getaway. I highly recommend Samuel & Catherine’s cabin and will be coming back in the near future.

Private Woodstock Getaway w Hot Tub
We had a wonderful stay at Marta's house. Everything was spotless, well cared for and thoughtful. The check in process was so simple and the house rules were easy to follow. The record collection was such a nice touch, especially on a rainy Saturday afternoon and the basement with a full media setup and games was perfect for a Saturday night in. The beds were comfortable, plenty of towels and amenities and the hot tub was great as well! The location was also great! Nothing bad to say about this amazing little spot :-)
Quick stats about vacation rentals with a kayak in New Fairfield
Total rentals
30 properties
Nightly prices starting at
G$27,189 GYD 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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- Fairfield Beach
- Yale University
- Rye Beach
- Yankee Stadium
- Rye Playland Beach
- Bronx Zoo
- Minnewaska State Park Preserve
- Walnut Public Beach
- TPC River Highlands
- Bethpage State Park
- Thunder Ridge Ski Area
- Woodmont Beach
- Ringwood State Park
- Rye Town Beach
- Seaside Beach
- Bushnell Park
- Calf Pasture Beach
- Jennings Beach
- Silver Sands Beach
- Bash Bish Falls State Park
- Sunken Meadow State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Centerport Beach