
Holiday rentals with a kayak in Philipstown
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Top-rated Accommodation with a Kayak in Philipstown
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Holiday House Rentals with a Kayak

Creekside Cottage
We had a great weekend stay at Katherine’s. The Esopus Bend Nature Preserve is only a ten minute drive and we really appreciated the local recommendations provided in the binder!

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.

Beaver Lake Escape
Clean and comfortable cottage across the street from a lovely small lake. Good communication, easy to find. Enjoyed walking the pups around the lake. Plenty of wildlife (deer, ducks) around.

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!

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

*Waterfront Modern Home w/Hot Tub and Fast Wifi
Mixing business with pleasure, we prefer to stay in an Airbnb versus hotel. Jack’s place offered us the home away from home we were looking for. The beds were very comfortable and the home was nice and clean. After a days work, we enjoyed soaking in the hot tub. Looking forward to the next trip.

Wander Inn! Golf Sim, Hot Tub, Pools, Lake
Heather was very interactive with my stay and gives very clear instructions! The house is exactly as described and photoed! Fun activities to do at home and very clean! Plenty of space in the house with a great kitchen! Definitely would stay again and recommend to friends/family!

Dancing Feather: Cozy Lake-Front A-Frame Chalet
Perfect place for a long weekend with our family. Plenty of space for the 5 of us and an absolutely beautiful location. Right on the water with access to multiple kayaks. Very peaceful setting with easy access to nearby towns like Monticello and White Lake.
Cottages 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!

Romantic Private Lake Art-Deco Cabin Hudson Valley
The area was absolutely beautiful. Valhalla Lake was private with stunning views. The cabin was exactly as it was described and the book of directions that was left for guidance was easy to follow.

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.

Driftwood Cottage on Welcome Lake-peaceful retreat
Pleasant couple very nice and courteous thank you for opening your beautiful peaceful home up to us we will definitely be back . Thank you again for lending us your boat my first experience and I love it and Chris loved every moment for her bday she loves fishing . Your house is amazing looking forward to our next stay already lol.

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.

Upper Delaware River cottage
My wife and I were looking for a relaxing, peaceful place to spend our wedding anniversary and John’s place more than delivered. The grounds were beautiful and the views were breathtaking. The house was clean and cosy with large windows for letting in the sunlight and fresh air. The sounds of the river were incredibly calming. Leave the white noise machine at home and let the river sing you to sleep! Our dog had plenty of room to run around the property and she loved daily visits to the river, as we did too. The nearby town had some nice restaurants that John recommended, the Heron being our favorite! We had everything we needed and plenty of accommodations were provided, but it was clear that if you needed anything, John would make it happen for you. We loved this place and would absolutely stay there in the future.

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard
Very nice peaceful places and very good service i will definitely be back soon, thank you
Cabin rentals with a kayak

Lake Front Catskills Lodge
Absolutely gorgeous place. Was so peaceful and nice. Meghan was friendly and responded very fast when we needed something. Would love to come back and enjoying the kayaks on the beautiful lake again!

Charming Catskills Lakefront Home—2 hrs from NYC!
Jill’s place was beautiful , cozy and unique. She was very accommodating with any questions we had, and the area had lots to offer. We drove through the mountains, checked out the historic Woodstock grounds, and went to many of the really cool breweries that were suggested. We also really enjoyed playing many of the records that she had while enjoying sunsets from the lake view of the house. Definitely would recommend and would love to come back for a visit

Lake Access•Canoe•Paddle Boards•Renovated•BBQ
Really charming cottage in the woods, and great, responsive hosts. Really had a nice time in this wooded and rural area, with two lakes nearby and the canoes on white lake. The cottage was clean and had a sleek, minimalist, scandanavian style (I felt like I was back in Sweden from years ago), which we appreciated! very peaceful at night and the AC worked great which helped out greatly on the hot days we were there. It's close enough to Woodstock museum/grounds, good food and laid back entertainment options in neighboring towns. Overall, a great stay, thank you!

Tranquil Lakefront Cabin!
Very nice house, good fishing and wildlife nearby. A little closer to the neighbors than expected, but overall a great place and would love to come back

Narrowsburg Lakefront w/ Hot Tub, FP, Pet Friendly
House sits right on the lake, beautiful property very private but close to town. The open floor plan is so comfortable. Kitchen is well stocked with everything you could need. The house was well organized and very clean. Communication with Anna was easy and very responsive. The hot tub was such a nice treat at the end of the day. Would highly recommend this home.

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.

Log Cabin * Hot Tub * Sauna * 4.6 mi. Bethel Woods
Julie's place was the perfect winter getaway. The fireplace, hot tub and sauna warmed us and the very well-equipped kitchen enabled us to prepare great meals. The house was beautiful, with two living rooms for different activities and energy levels, a game room downstairs, a dining room with a large table and chairs, and comfortable furniture and beds throughout. Julie texted me to make sure that our every need was met. We had a snow and ice storm, and she had the driveway and walkways plowed, shoveled and sanded twice, and kept plenty of salt on-hand. We hope to return sometime in warmer weather so we can enjoy the pond, too.

Gorgeous Lake Front cabin with Hot tub and Kayaks
Beautiful hidden property tucked down off of road. The place has everything you need and is so quiet n peaceful. The hot tub was great to relax in and was nice to see deer morning n evening grazing.
Quick stats about holiday rentals with a kayak in Philipstown
Total rentals
10 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
1.4K 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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- Times Square
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