
Vacation rentals with a kayak in Philipstown
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Top-rated kayak rentals in Philipstown
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House rentals with a kayak

Lakehouse Woodland Retreat
My family and I really enjoyed Elizabeth property very comfortable and quiet, we definitely thinking about coming back soon.

Spacious Catskills Retreat w/Game Rm/Fenced/Deck
Great place to stay with family, plenty of room. Kids enjoyed the fishing and kayak. This lake house was very clean and well stocked with essentials. Fenced in yard was great for the dog.

🛶 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!

Waterfront Ranch on The Delaware River
Krystyn was very responsive with any questions that we had. The place is beautiful and very peaceful. We didn't need to text Krystyn once during our stay there because anything we needed was provided. Our family had an amazing and very relaxing weekend. We would definitely come back here again.

Lakefront/boat dock/deep water!
Evelina was extremely communicative and flexible with our group - we had a lovely time.

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 ✨

Cozy and quiet lake front cottage with firepit
We had a lovely, relaxing stay at the lake house. The interior felt welcoming and homey, and we enjoyed the peaceful setting of the lake house. There were nice views down to the lake, and we really liked the layout of the bedrooms which were separated nicely for privacy from each other, while being close enough for the kids. The beds were comfortable and there were plenty of toiletries. The kids were delighted to climb the ladder to the loft and spent plenty of time up there. The kitchen was well stocked, with probably more pans and gadgets than we have at home. Appreciated the s'mores kit, which the kids toasted up. We enjoyed the outdoor fire, which had plenty of seating and a nice supply of wood. The highlight was definitely the time we spent on the lake. We got out in the pedal boat and kayaks. The kids enjoyed exploring a deserted island and watching some lake wildlife as we spent time on the water. Thanks for a wonderful stay!

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.

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.

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.

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK
We had a lovely time staying at Jo and Sean’s place even though it was the off season. One big thing for us is that our 3 dogs were welcomed with no restrictions. We enjoyed the deck being enclosed and having the dog run accessible. The views of the lake were stunning and peaceful. Our hosts were the most responsive we’ve ever had. Before we came, they provided lots of ideas for places to visit and things to do. We hope to come back again!

Oscaleta Guest House: Lakefront Cabin
T’s house perfectly matches my expectations, his hospitality and responsiveness went beyond satisfaction, everything inside the house is clean and full of details, the view and surroundings the house is breathtaking. We enjoyed very much for our stay. This house now has a special meaning for us, we will definitely come back! For anyone interested: T is one of the best hosts I’ve met, you will be amazed and impressed.
Cabin rentals with a kayak

Lake Front Catskills Lodge
We had an absolutely amazing stay at this cozy cabin by the lake! The location is perfect, peaceful, scenic, and surrounded by nature. One of the highlights was waking up to deer grazing right in the backyard. It felt like a nature retreat, and we loved just sitting on the porch with chai, watching them wander by. The cabin itself was clean, comfortable, and well-equipped with everything we needed for a relaxing getaway. The kitchen had all the essentials, and the living space was super cozy, especially with the fireplace going in the evening. The cabin is perfectly nestled right by the lake, which is literally in the backyard, such a dream to wake up to that view every morning. The fire pit was another highlight, we spent our evenings roasting marshmallows, sharing stories, and stargazing. A huge shoutout to Meghan, the host, she was so helpful and kind! She shared a bunch of local spots to check out. We’re already talking about coming back again!

Charming Catskills Lakefront Home—2 hrs from NYC!
Jill’s home was a perfect escape from city life. You might lose cell service but it felt great to unplug from a busy schedule. Jill leaves a book of towns, trails and activities to check that was very helpful when my group wanted to leave the house and explore the towns a bit. Definitely would love to come again in the summer to enjoy the lake access.

Canoe•Lake Access•Paddle Boards•Renovated•BBQ
My boyfriend and I had a lovely time at Melinda’s place! It is so cozy, the esthetic is so nice. It was clean and private and quiet. We had everything we needed in the kitchen and throughout - the water pressure in the shower was amazing! We saw deer every day, we went on lots of walks and the neighbors were all friendly. I misunderstood from the pictures, and thought the cabin was directly next to the lake, but it was in walking distance. We would definitely come back, it was so lovely!

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.

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!

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 !

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!

Cozy Catskills Cabin
Wonderful stay beautiful house , the sunroom gives you an opportunity to relax among nature which was exactly what we were looking for during this getaway would love to return during warmer weather. The record player was a nice touch I even found a record with a song titled just like my full name crazy coincidence was nice to spend my bday listening to these old records. Thank you so much for bring a great host !
Quick stats about vacation rentals with a kayak in Philipstown
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ184 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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- Radio City Music Hall
- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Tenement Museum
- Riverside Park
- Mountain Creek Resort
- Comedy Cellar
- Apollo Theater
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- MetLife Stadium
- Inwood Hill Park
- United Nations Headquarters
- Bronx Zoo
- Astoria Park
- Rockefeller Center
- Minnewaska State Park Preserve
- The Metropolitan Museum of Art
- Central Park Zoo