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

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.

Perfect New Paltz Location!
We loved staying at this house! I gathered up good friends for a birthday weekend of art, biking, visiting a winery for music, and spending precious time together. The three bedrooms and two baths were perfect. One of my friends enjoyed the big bathtub! We loved the open great room with the windows towards the mountains. The host was super kind and responsive to my questions. I am still smiling and would recommend this place whole heartedly.

Adorable quiet & cozy lakefront studio on dead end
We had a great time at Luz’s place. She was very responsive and proactive. The place itself is perfect for a couple and the views/lake access are the biggest perk. Very close to many great restaurants (all within a 7 min drive) and not far from other great places if you don’t mind driving a bit further. It was the perfect place for a long weekend and we hope to be back soon!

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!

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.

Boonton Revival- A restored treasure in NJ
Eugene’s place met all our needs — bedrooms comfortable, backyard great. Eugene interesting and kind. Thank you!
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!

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.

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!

Cozy Getaway | Pet Friendly | Litchfield Cty
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.

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.
Cabin rentals with a kayak

Dekeman Acres Cabin
We stayed over Memorial Day Weekend, '25. Wanted a quiet getaway for the four of us: my wife and myself, plus our adult daughter and our high school aged daughter. This property delivered. Quiet mix of woodlands and farm. Babbling brook right outside the back door. And it was a short drive to Delhi, which was a lovely little town.

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

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

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.

Wonder's Never Cease: Hot Tub, Sauna & Cold Plunge
Amazing stay with incredible amenities! The house was super clean and spotless upon arrival. Beautiful property - you won’t want to leave! The host is super accommodating and provides thorough instructions for the amenities. Wonder is a thoughtful host and prepares you with all the tools/info you need to make your stay perfect. We used all three of the hot tub, cold plunge and sauna - it’s an immaculate setup. It rained most of our stay and the amenities kept us happily preoccupied all weekend.

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.

Lakeside Cottage: Boulder's Bluff
We loved our stay at Ed's cabin. it is a real gem and perfect for a long weekend away. we loved the fireplace, the rocking chairs, the windows with views out onto the lake that make you feel like you're right over the lake and in the trees. there were nice restaurants and hikes in the area, but we were perfectly content watching the lake and reading from the cabin. Ed was perfectly accommodating and extremely generous with his space, couldn't recommend more highly.

Country Cabin on 115 acres Cabin #2, with WiFi
Stanzonis Cabin #2 was a perfect getaway to both enjoy a concert at Bethel Woods (minutes away!) and enjoy some family time with our three younger kids. The Lake Huntington access and area Stanzonis has set up was fantastic! Such a nice bonus of staying with them. We lucked out with weather so we had the wonderful ability to enjoy the grounds and even have a fire in the pit. Tons of fire wood on the property to pull over and keep it going for hours. SO relaxing! Would definitely stay here again!
Quick stats about holiday rentals with a kayak in Philipstown
Total rentals
10 properties
Nightly prices starting at
₹4,308 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
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Fairfield Beach
- Rye Beach
- Citi Field
- Mountain Creek Resort
- MetLife Stadium
- Yankee Stadium
- United Nations Headquarters
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- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Bronx Zoo
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- One World Trade Center
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