
Vacation rentals with a kayak in Philipstown
Find and book unique kayak rentals on Airbnb
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$10,459 GYD per night before taxes and fees

Verified guest reviews
Over 1,240 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!
Top-rated kayak rentals in Philipstown
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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
4.99 out of 5 average rating, 140 reviews
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
4.99 out of 5 average rating, 191 reviews
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.
4.89 out of 5 average rating, 332 reviews
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🐕
4.99 out of 5 average rating, 209 reviews
Hot Tub * Private Dock * Quiet Lake Home
Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages
4.99 out of 5 average rating, 114 reviews
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.
4.94 out of 5 average rating, 144 reviews
Hilltop Retreat- Lakefront with Dock
Enjoy all that Candlewood Lake and Squantz Pond State Park have to offer in the comfort of our home. Come reconnect with love ones and relax in the serene surroundings. This waterfront property has a private dock, features 2 bedrooms, 2 full baths, and views from almost every room in the home, plenty of indoor and outdoor entertaining space and a wood burning fireplaces to keep toasty during chilly evenings. Toiletries, all linens are provided. Please read house rules before booking.
4.95 out of 5 average rating, 105 reviews
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 two-person kayaks are available for use from May 1 to November 1.
4.96 out of 5 average rating, 463 reviews
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
4.97 out of 5 average rating, 117 reviews
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.
4.99 out of 5 average rating, 190 reviews
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
4.96 out of 5 average rating, 252 reviews
Charming Hudson Valley Lakefront Escape with Views
A year-round waterfront home with gorgeous unobstructed views of Whaley lake provides the perfect escape for a long weekend or vacation. Enjoy swimming and lake activities via private direct lake access. Spacious boathouse deck for entertaining or sunbathing. Cozy up to a two-story stone fireplace while enjoying the fall and winter colors. Just 10 minutes from Thunder Ridge Ski area.
4.87 out of 5 average rating, 134 reviewsPopular amenities for Philipstown kayak rentals
House rentals with a kayak

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
4.96 out of 5 average rating, 141 reviews
Comfortable & Spacious Country Home - All Seasons
4.98 out of 5 average rating, 123 reviews
Perfect New Paltz Location!
4.98 out of 5 average rating, 158 reviews
Riverfront Stone Cottage Private/ hot tub/ boats
4.91 out of 5 average rating, 306 reviews
Waterfront Cottage - Hot Tub, Kayaks and Fire Pit
4.95 out of 5 average rating, 109 reviews
Beautiful Lakefront Views! Beach, Firepit + Kayaks
4.95 out of 5 average rating, 240 reviews
Stylish Lakeside Cottage with Hot Tub
4.96 out of 5 average rating, 332 reviews
Waterfront, Dog & Family Friendly, Cozy Cottage
4.96 out of 5 average rating, 154 reviewsCottage rentals with a kayak

The Mountaintop Lakehouse that Time Forgot.
4.97 out of 5 average rating, 391 reviews
Lakefront House w/Private Dock, Fire Pit & Hot Tub
4.98 out of 5 average rating, 178 reviews
Oscaleta Guest House: Lakefront Cabin
5.0 out of 5 average rating, 141 reviews
Romantic House on a Magical Lake
4.91 out of 5 average rating, 210 reviews
Historic Gem in Culver Lake. (Branchville NJ)
4.97 out of 5 average rating, 108 reviews
Spacious Lakefront House With a Private Dock
4.87 out of 5 average rating, 126 reviews
Heron's Hideaway: Stylish Lakefront 5 BR Home
4.96 out of 5 average rating, 123 reviews
1 Bed Pond Cottage w/ pool/hot tub/sauna access
4.88 out of 5 average rating, 112 reviewsCabin rentals with a kayak

Little Lake Cabin— Lake Access, Hot Tub & Kayaks
4.96 out of 5 average rating, 409 reviews
Riverfront Retreat | Hot Tub, Firepit & Pool Table
4.97 out of 5 average rating, 128 reviews
Lakeside Cottage: Boulder's Bluff
5.0 out of 5 average rating, 249 reviews
Cozy Lakefront Catskills Cabin—2hrs from NYC!
4.92 out of 5 average rating, 302 reviews
Design-Forward Riverfront Cabin on 120 Acres
4.96 out of 5 average rating, 139 reviews
Lakefront • Hot tub • Kayaks • Fire Pit • Fishing
4.94 out of 5 average rating, 215 reviews
ECHO cabin - lakefront peaceful modern house
4.84 out of 5 average rating, 148 reviews
Magical LAKEFRONT Cabin
4.92 out of 5 average rating, 131 reviewsWhen is the best time to visit Philipstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$56,477 GYD | G$57,732 GYD | G$56,268 GYD | G$64,425 GYD | G$98,730 GYD | G$87,644 GYD | G$76,139 GYD | G$91,409 GYD | G$63,589 GYD | G$67,145 GYD | G$63,798 GYD | G$63,170 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 |
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- Times Square
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