
Holiday rentals with a kayak in Philipstown
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Philipstown
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
Perched on the water’s edge, you’ll look down from this bright, modern post at an expanse of winding river and broad tree-lined meadows. Let the mellow current and enveloping natural setting satisfy and soothe your senses. This special place is close to everything, making it an ideal launchpad to all the Hudson Valley has to offer. Kingston, New Paltz and Rosendale are all ten minutes away, surrounding you with a plethora of hiking trails, climbing, dining, drinking, entertainment and shopping.

Beaver Lake Escape
Welcome to Beaver Lake Escape! This one bedroom, one bathroom lakeview home has all of the amenities you will need for a relaxing vacation getaway! Come experience a warm & cozy environment with full access to the community beach where you can enjoy kayaking, swimming and fishing (catch & release). You'll also find great hiking in the Spring, Summer and Fall at the Neversink Gorge Unique Area and skiing/snow boarding in the winter at Holiday Mountain! Only a 25 minute drive to Bethel Woods!

Lakefront Cottage near Hudson Valley
Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Cozy Winter Lake Cabin
Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes COMPLIMENTARY Firewood, NO CLEANING/PET FEES🐕

Lakefront Escape: Beach Access, Firepit, Kayaks!
SUMMER AT THE LAKE! You'll love this beautiful 3BR home in Greenwood Lake just steps from the beach! Experience AMAZING lake views & tranquil atmosphere. Enjoy free kayaks, canoe, paddle board and beach access! Huge wrap-around deck with firepit, ping-pong, and great outdoor living space. Inside has a well-equipped kitchen & all new furniture. This hideaway promises memories that will last a lifetime! Nearby wineries, breweries, restaurants, Warwick Main St, hiking, & more! ~ 1 hr from NYC

HEAVEN ON EARTH - Hudson Riverfront Home
Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Twin Lakes Designer A-frame Stone Cottage
*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Private Lake House 1 Hour to NYC & Near Westpoint
Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Lakeside Cottage: Boulder's Bluff
Come enjoy the serenity of our renovated lakeside cottage! Guests can enjoy their time relaxing fireside with panoramic views, hiking or biking 22 miles of trails running through our backyard, and let's not forget splashing around in the lake. We are sorry but we are unable to accommodate pets. Pack N Play available only when request ahead of time. Pack N Play sheets not provided.

Hudson Valley Lakefront Cottage | Nature Escape
Escape to this tranquil, lakefront cottage in the Hudson Valley. Enjoy stunning lake and cascading creek views, kayaks, paddleboards, a firepit with a steady supply of firewood for cozy evening fires, two Weber grills, and an on-site Level 2 EV charger. Ideal for couples, small groups, or intimate gatherings seeking a peaceful retreat surrounded by nature.
Popular amenities for kayak rentals in Philipstown
House rentals with a kayak

Perfect New Paltz Location!

Creekside Cottage

Magical Waterfront Escape on the Esopus Creek

Entire lake house to yourself. Great for groups

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

15% off, fireplace, workcation spot, private pond

Cozy & Spacious Country Home - All Seasons

*Hot Tub* Kayak*VIEWS* Stylish Waterfront Retreat
Cottage rentals with a kayak

Cottage with Private Deck on 8 acres of Woods

Waterlily Lakehouse - Modern+Waterfront+Retreat

Be in Nature at this Gorgeous Riverfront Cabin

The Mountaintop Lakehouse that Time Forgot.

Charming Fairfield Beach Cottage

Lakehouse, Sunset View, Big Deck, Hot Tub, Dogs OK

Heron's Hideaway: Stylish Lakefront 5 BR Home

Oscaleta Guest House: Lakefront Cabin
Cabin rentals with a kayak

Cozy Lakefront Catskills Cabin—2hrs from NYC!

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Canoe—SUPs—Innertubes—Chic—Renovated—Fire Pit—BBQ

Tranquil Lakefront Cabin!

The Little Lake Cabin w/ hot tub, kayaks & firepit

Cozy Cabin with Pond on Six Acres

Design-Forward Riverfront Cabin on 120 Acres
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £167 | £178 | £196 | £203 | £251 | £291 | £268 | £322 | £224 | £237 | £225 | £223 |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about holiday rentals with a kayak in Philipstown

Total holiday rentals
Explore 10 holiday rentals in Philipstown

Nightly prices starting at
Philipstown holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,160 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
10 of Philipstown holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Philipstown rentals

4.9 Average rating
Philipstown stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Fitness-friendly rentals Philipstown
- Waterfront rentals Philipstown
- Rentals with a fireplace Philipstown
- Rentals with a patio Philipstown
- House rentals Philipstown
- Rentals with a hot tub Philipstown
- Rentals with outdoor seating Philipstown
- Rentals with a firepit Philipstown
- Family-friendly rentals Philipstown
- Flat rentals Philipstown
- Rentals with an EV charger Philipstown
- Pet-friendly rentals Philipstown
- Rentals with breakfast Philipstown
- Rentals with pools Philipstown
- Rentals with a washing machine and dryer Philipstown
- Rentals with beach access Philipstown
- Rentals with lake access Philipstown
- Rentals with a kayak Putnam County
- Rentals with a kayak New York
- Rentals with a kayak United States
- Times Square
- Madison Square Garden
- New York City Center
- New York University
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Mountain Creek Resort
- Yankee Stadium
- Bronx Zoo
- United Nations Headquarters
- Rockefeller Center
- Brooklyn Bridge
- Citi Field
- Empire State Building
- Grand Central Terminal
- Bryant Park
- Radio City Music Hall
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- The Metropolitan Museum of Art
- Fairfield Beach
- Astoria Park
- Prudential Center




