
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

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.

Creekside Cottage
We had the best long weekend, the house is immaculately clean and so peaceful. Enjoyed sitting in the screened in porch looking out at the water. Wish we could have stayed longer! The area is beautiful, lots to do. Would definitely go back for another stay!

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
Our stay at Rich’s place was very pleasant, despite the fact that we had rain the whole time we were there. We enjoyed using the hot tub and the grill for cooking, and liked the peace and quiet. Rich and Brianna are very responsive and helpful hosts. I would definitely recommend the place to others if staying in this area. We would like to return in the future when the weather is better!

Artsy and stylish home with big yard.
We loved staying at Bengisu’s home for the holidays. It’s even cozier and more welcoming than can be seen in photos, and the location is great - just a few minutes walk into town to enjoy everything Beacon has to offer. Bengisu was communicative and helpful leading up to the trip, and her home was the perfect place for us to spend a few days relaxing and exploring. We would absolutely stay here again on a future trip.

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 was very responsive host and attentive. Ensure placed was cool for arrival since we were checking in late. When we had an issue he was very responsive and quickly addressed it. Overall place is nice and walkable to boonton historic with plenty of coffee shops & restaurants. Plenty of amenities and he put a lot of effort in ensuring you have a great stay. Weather was typical June rain so we did not get to enjoy the beautiful koipond. However you can see it from office, kitchen and bathroom. Highly recommend this place just note that bedrooms and bathroom are all upstairs.
Cottage rentals with a kayak

Cottage with Private Deck on 8 acres of Woods
The stay at Ashlie’s was just perfect. The cabin is so intimate and secluded, but very close to everything you might wanna check out! Ashlie was very friendly, I would definitely stay again!!

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.

Sunset Cabin Modern Home Kayak FirePit Lake Access
Great place to stay - easy instructions to follow, house is even more spacious than it looks in photos, and the backyard is GREAT for dogs. Would definitely recommend.

The Mountaintop Lakehouse that Time Forgot.
Surprised my girlfriend with a weekend get away for her birthday and she was thrilled. Evelina and John are great host and their place is warm and welcoming. We loved the lake, and the quiet serenity of the location is perfect for a weekend trip from the city. Also loved the kitchen which made cooking in a breeze because how thoughtfully organized it was. Although our stay was short we did find time to take the canoes out explore the lake and take a refreshing dip. Our only complaint was that our stay wasn’t longer, and we’re both looking forward to coming back !

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.

Upper Delaware River cottage
It was an incredible experience. My family, my two dogs, and I thoroughly enjoyed our stay. Upon arrival, we were greeted by our wonderful and attentive host, John, who helped us carry our bags and belongings to the cabin. The house is a cozy 1930s cottage, nestled on a hill in a green meadow, offering peaceful views in a pristine and tranquil setting overlooking the Delaware River which was directly in front of the house. The house features beautiful antique furniture, a well-equipped kitchen, and comfortable beds. We especially liked that the house was dog-friendly. It was a haven for them! It was amazing to see marmots, deer, eagles, and birds of various species, which were all part of our enjoyment. We will definitely consider staying here again and highly recommend this place to anyone looking to relax and be in touch with nature. Thanks again for allow us to stay in this wonderful Place, John!

Lakefront Getaway 1 Hr from NYC
I stayed for a month solo to focus on my projects & it was the most peaceful month. The house is contained in nature with a plethora of birds & animal life that I witnessed.. a crane fishing at the creek beside the house as I worked, a pair of woodpeckers hunting at the lawn, a chipmunk that lives under the house & has a morning ritual of its own. All while the lake boasted breathtaking sunsets. On the practical side, the kitchen was fully equipped with everything one needs to cook everyday, which I did. It was private & safe for a solo girl like me to stay a month. Amazon found its way to it no problem. And there are nice streets to take long walks which I did 1 hour a day. Very friendly neighbors, everyone waves at ya. The covered patio, working from the dinner table, waking up in the bedroom to the lake.. all main areas are flanked by beauty. Really was perfect for a solo getaway. Also wifi was very reliable. Keep in mind lake living = insects. They’re harmless. Highly rec renting!
Cabin rentals with a kayak

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
W’s place is great for a large family or group of friends looking for a getaway in a peaceful, private, retreat-like environment. The house has cozy Catskill cabin vibes with a well equipped kitchen, comfortable beds, updated bathrooms and a variety of different spaces to provide a large group with opportunities to spread out and find quiet nooks and crannies when needed. The beautiful wooded setting is perfect backdrop for all the amenities — wood fired hot tub and sauna plus cold plunge make the property feel like a private spa. It’s very easy to stay on the property for a full day without leaving, however there’s also an abundance of local adventures to be had — hiking, swimming, fishing etc. Great place for outdoor enthusiasts. W is responsive and helpful in his communications.

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
My partner and I couldn’t have enjoyed our stay more. The cabin is tucked away, but Edward’s clear instructions made getting there a breeze. It was spotless, thoughtfully stocked, and we felt genuinely cared for. The lake water was crystal clear, with wildlife all around. We took full advantage of the kayaks, rowboat, floats, and fishing gear, and ended each evening watching the sunset from the dock. The neighboring cabin was occupied by Edward’s family, but they were kind, helpful, and never intrusive—actually, their presence added a sense of comfort in such a secluded spot. It was the perfect weekend escape. We hope to be back soon! Thank you, Edward!

Country Cabin on 115 acres Cabin #2, with WiFi
My dad and I stayed in cabin # 2 for a night after competing in the Spartan Race in Bethel. It was the perfect place to wash all the mud off, grab a bite and rest our heads before driving home. The lake was perfect for my dad to fish and for me to read my book while he caught his biggest fish yet. The cabin was cozy and clean with very comfortable beds and couches with a rural upstate feel. Thanks a bunch!

The Cabin at Pleasant Valley Farm
This place was a homerun. Clean organized great location peaceful. Nice detail and accessories provided for a stay at a log cabin. Me and girlfriend already booked it again Excited to go back.
Quick stats about vacation rentals with a kayak in Philipstown
Total rentals
10 properties
Nightly prices starting at
R887 ZAR 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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