
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
This is a wonderful stay if you are traveling with kids and pets. So much to do in the amazing basement. The property is fully fenced, allowing your doggo the freedom to roam! Great location. Plenty to do around town.

🛶 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!

Entire lake house to yourself. Great for groups
Scott's place was great. We were so relaxed and felt right at home. We will be going back which is the best compliment I can give an AirBnB. The views were beautiful!

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!
Very happy with the experience. There are stairs to get to the house but the house is as advertised and the owner was considerate and communicated well. We would return.

Aster Place
the hosts were incredibly welcoming and attentive, ensuring we had everything we needed for a comfortable stay. the windows provided plenty of natural light and showcased the beautiful lake just outside. would love to come back in the summer to enjoy some more outdoor activities nearby :)
Cottage rentals with a kayak

Private Lake House 1 Hour to NYC & Near Westpoint
Our family really enjoyed our stay at this lake house. To wake up every morning to the gorgeous view of the lake and enjoy the surroundings created for a very relaxing trip. The house was well stocked with toiletries, towels and the coffee/tea station was a hit with our family. Would definitely come again, if in the area.

Cottage with Private Deck on 8 acres of Woods
This was one of the most magical little cabins me and my partner has stayed in!

Cozy and quiet lake front cottage with firepit
My family and I rented Ava’s home over Christmas and it was the best AirBnB experiences I’ve ever had. The house was very well stocked and truly had everything we needed. We had a 5 year old with us and she loved all the toys available. The space was truly beautiful and Aga was responsive and proactive with everything. We knew just what to expect. Truly above and beyond a 5-star experience-we hope to find an open time this summer to return!

Be in Nature at this Gorgeous Riverfront Cabin
lovely cottage that is beautifully designed. loved the comfortable beds and chairs. thanks Mark for a great stay.

Romantic House on a Magical Lake
My family and I had a wonderful time at Gisela's lake house!! Her house was clean, cozy, and felt like home. Gisela was incredibly responsive, the property was very clean, and the views were amazing!! Checking in and out was quick and simple. The house is on the main road and only a few minutes from Kingston and is central to anywhere in the Catskills or Hudson Valley. I would recommend to anyone looking to enjoy the area.

Lakefront Cottage near Hudson Valley
Tony’s cabin is a perfect lakeside escape. The space is clean, well-designed, and bright with natural light. The fireplace is huge and beautiful. The large windows overlook the lake. A deck leads down to the little lakeside area where there are stand-up paddle boards and kayaks. The neighborhood is quiet and walkable with a nice beach area about 10 minutes from the cabin. Cold Spring is 20 minutes away and has yoga classes, great massages, coffee shops, and restaurants. There are seemingly endless hikes within 20 minutes drive of the cabin. We hiked a different park every day. We had the best time relaxing in the cabin and enjoying the beautiful surrounding area!

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK
Took a weekend trip with my family and it was such a beautiful and peaceful time. The view was amazing, the house felt comfortable too. The host was very responsive and attentive which was a bonus. We would definitely come back!

Oscaleta Guest House: Lakefront Cabin
The cottage is exceptional in every way. It’s stylish, cozy, efficient, and well thought out. The hosts that rent it are the icing on the cake though! We took advantage of all the opportunities for fun; canoe, fire pit, long walks, coffee on the patio, incredible nature watching, yoga, and meditation! You’ll want to move in as soon as you see it. The views from the main window are top notch! T and Karen really made the experience memorable and were more than accommodating, friendly, and all around good humans. Thank you!!!!
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!
My friends and I did a staycation for a weekend at Jill’s beautiful Airbnb. The place was very beautiful and comfortable! Jill was very proactive in sending information and very quick responding when we had a question. Definitely planning on going back!

Canoe•Lake Access•Paddle Boards•Renovated•BBQ
A beautiful place to stay, very quiet and clean, just wasn’t accustomed to no curtains but got adjusted to pretty quickly. Felt as if it were my own home at some point. Would stay again

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
We enjoyed our 3 night stay at Marta’s place. It had everything we needed, clean comfortable beds, kitchen with all necessary equipment, clean and modern bathrooms, a lot of games and books, a cozy living room with a fireplace that created the best atmosphere. We spent our time playing games with the kids, relaxing and cooking. The place is definitely recommended and super close to stores, restaurants, just a quick drive to center of Woodstock. Thank you Marta 🙏

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
Destinations to explore
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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
- Inwood Hill Park
- MetLife Stadium
- Bronx Zoo
- Astoria Park
- United Nations Headquarters
- Rockefeller Center
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Central Park Zoo