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

Lakefront Escape! Views, beach, Firepit & Kayaks!
SUMMER AT THE LAKE! You'll love this cozy 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, & great outdoor living space. Inside has a well-equipped kitchen & all new furniture. This beautiful hideaway promises memories that will last a lifetime! close to wineries, breweries, restaurants, Warwick Main St, hiking, & more! Permit #P25-0394

Modern Nordic Designed Cabin
Newly designed Modern Nordic Cabin. Escape to the tranquility of the mountains and lakes. The Nordic cabin is modern with high-end finishes throughout. The open concept living area features a fireplace, waterfall shower, vaulted ceilings, and large windows that offer stunning views of the surrounding forest and lake. Getting to and from NYC is easy. There is a bus stop down the street and a train station 15 minutes away. Perfect for a convenient getaway from the city Warwick town Permit 34469

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

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 Lake Cottage
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 in any temps from inside or out, or coffee in the tree hut! 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🐕

Oscaleta Guest House: Lakefront Cabin
Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

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..

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC
Escape to our modern, year-round lakeside paradise on Greenwood Lake, just 1 hour from NYC. This bright, airy home offers stunning lake views, a private dock, and a sandy beach area. Perfect for families or couples, enjoy seasonal activities from swimming and kayaking in the summer to skiing just 10 minutes away in the winter. Relax by one of two fireplaces or on the spacious deck. A tranquil retreat for relaxation and adventure. Permit N. 23-225

Little Lake Cabin with Hot Tub, Kayaks & Fire Pit
Named one of the best Airbnbs in Connecticut by Business Insider, The Little Lake Cabin is a cozy wooded retreat minutes from Candlewood Lake with a year round hot tub, fire pit, and kayaks to take out on the lake. Perfect for couples getaways and relaxing weekends, the cabin is close to hiking, boating, wineries, antique shops, skiing, and charming New England towns. End your days soaking in the hot tub and relaxing by the fire under the stars.

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.
Popular amenities for Philipstown kayak rentals
House rentals with a kayak

The Getaway: Beautiful Waterfront - New Milford CT

Creekside Cottage

Magical Waterfront Escape on the Esopus Creek

Adorable quiet & cozy lakefront studio on dead end

Twin Island Lake House • Hot Tub

Entire lake house to yourself. Great for groups

Lakeside Lodge with Studio Apt

*Waterfront Home w/Hot Tub, Kayaks and Fast Wifi
Cottage rentals with a kayak

Waterlily Lakehouse - Modern+Waterfront+Retreat

Be in Nature at this Gorgeous Riverfront Cabin

The Mountaintop Lakehouse that Time Forgot.

Cozy Cottage |Quintessential CT | Pet Friendly

Upper Delaware River cottage

Roscoe Cottage Pet Friendly

Heron's Hideaway: Stylish Lakefront 5 BR Home

2 Per. Rain Shower-Cozy Cottage-King-Firepit-Kayak
Cabin rentals with a kayak

Cozy Lakefront Catskills Cabin—2hrs from NYC!

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing

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

Tranquil Lakefront Cabin!

Neighborhood Beach, Paddle Board, Swim

Log Cabin * Hot Tub * Sauna * 4.6 mi. Bethel Woods

Design-Forward Riverfront Cabin on 120 Acres

Private Woodstock Getaway w Hot Tub
When is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$56,475 GYD | G$57,730 GYD | G$56,266 GYD | G$57,521 GYD | G$71,117 GYD | G$82,621 GYD | G$76,137 GYD | G$91,406 GYD | G$63,587 GYD | G$67,143 GYD | G$63,796 GYD | G$63,169 GYD |
| 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 vacation rentals with a kayak in Philipstown

Total vacation rentals
Explore 10 vacation rentals in Philipstown

Nightly prices starting at
Philipstown vacation rentals start at G$10,458 GYD per night before taxes and fees

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

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Philipstown vacation rentals include wi-fi 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!
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- Rentals with a kayak Putnam County
- Rentals with a kayak New York
- Rentals with a kayak United States
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