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Vacation rentals with a kayak in Philipstown

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Philipstown

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Cottage in Phoenicia

4.91 out of 5 average rating, 577 reviews

Romantic Getaway in Lovingly Restored Esopus Cottage

This cottage is perfect for relaxation, working remotely and as a hub for experiencing the majestic Catskills. Featured in Curbed NY, a travel magazine, as “The Best Vacation Rentals in the Hudson Valley," the Esopus Cottage has over 1500 five-star reviews. (Inquire regarding 1-night stays from Sunday to Thursday at a special rate!) As Superhosts for 10+ years, we are committed to stellar customer service and making your vacation a memorable and restorative experience. License # 2023-STR-055P

Jul. 15 – 22

$220 CAD per night

Cottage in Putnam Valley

4.9 out of 5 average rating, 214 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.

Nov. 11 – 18

$541 CAD per night

Guest favourite

Cabin in Huguenot

4.95 out of 5 average rating, 238 reviews

Tranquil Lakefront Cabin!

This Warm LAKEFRONT Home Grabs Your Soul and Forces you to Decompress Instantly. Enjoy the Large Well Appointed Screened Porch with Glass of Wine/Cup of Coffee as you Gaze over the Rustic Lake thru Stately Oak Trees and Cranberry Bogs. Boats Included!!! $50 Per Pet Per Stay… http://wpdh.com/airbnb-announces-hudson-valley-as-top-destination-in-the-world/?fbclid=IwAR32OGbKzPHj2WtVhQmXslZ9xZo9dNVnmp1nTL9mF_xOSaAFMDTnkhRsDA8 FOLLOW US ON INSTAGRAM https://instagram.com/tranquil_lakefront

Sep. 28 – Oct. 5

$236 CAD per night

Guest favourite

Cottage in Monroe

5.0 out of 5 average rating, 129 reviews

Cozy 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 abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Jul. 10 – 17

$761 CAD per night

Guest favourite

Cottage in Vernon Township

4.86 out of 5 average rating, 125 reviews

Dream Lakefront Home + Skiing near NYC

Stylish and very bright 3BR lakefront house with breathtaking views. The perfect stay for every season. Minutes away from Mountain Creek Ski Resort, Spa, and Waterpark, private beaches, golf courses, and hiking trails - Discounts for weekly and monthly stays. 3 bedrooms, 2 bathrooms. Huge terrace overlooking Highland Lake with grill and dining area and a very spacious dock with fire pit, private lake access, canoe, kayaks, and pedal boat, all included. Permit: 220004 Must be 21+ to book.

Mar. 4 – 11

$885 CAD per night

Guest favourite

Guest suite in Sherman

4.98 out of 5 average rating, 135 reviews

Cozy Scenic New England country retreat w/ hiking

Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.

Sep. 22 – 29

$266 CAD per night

Guest favourite

Home in Greenwood Lake

4.95 out of 5 average rating, 191 reviews

Stylish Lakeside Chalet with Hot Tub

Welcome to Greenwood Lakeside Chalet, an all-season waterfront retreat on beautiful Greenwood Lake (just over an hour from NYC) surrounded by the Sterling Forest and the Appalachian Trail Corridor. No car? No problem! Conveniently located just steps away from an express bus stop with regular service to/from Port Authority. Boating, Hiking, Fishing, Skiing, Breweries, Wineries, Apple Picking, Waterfront Restaurants, Shopping, Historical Sites, Golf - all nearby (or right in the backyard).

Nov. 6 – 13

$608 CAD per night

Guest favourite

Cabin in West Milford

4.98 out of 5 average rating, 110 reviews

Peaceful Lake Front Log Cabin w/3 bedrooms up to 7

Enjoy this peaceful lake front log cabin all to yourself and 6 more of family or friends! Sleeps 7. We are located just an hour from NYC. The cabin has recently been refinished with a new kitchen, appliances and all new furniture. Relax in our Lake front yard where you'll find a seating area with a firepit, large table for all your sunset dinners, a 2 person Hammock and a large BBQ. The cabin's location to many seasonal activities and events makes this an ideal year round destination!

Jan. 2 – 9

$628 CAD per night

Guest favourite

Guesthouse in Gardiner

4.99 out of 5 average rating, 136 reviews

Red Barn Retreat - Shawangunk Mountains Getaway

Our one-bedroom guest house offers serenity and privacy on the Shawangunk Kill river, surrounded by the natural beauty of local farmland and "the Gunks" mountains. Step outside to soak in the tub, kayak, enjoy a bbq, or gather around the firepit. When the spirit of exploration calls you, it's only a short drive to hiking, biking, and world-class rock climbing, along with wineries, breweries, farms, orchards, cider mills, and many fine restaurants. A retreat for body, mind, and soul.

May 29 – Jun. 5

$313 CAD per night

Guest favourite

Cabin in Sherman

4.97 out of 5 average rating, 310 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, SUP, two inflatable two person kayaks, and two wooden boats are available for use.

Jan. 30 – Feb. 6

$723 CAD per night

Guest favourite

Home in Greenwood Lake

4.97 out of 5 average rating, 147 reviews

Coldwaters: Hike, Wineries, Lake Access and Views!

Beautiful and comfortable home perched on a hill and across from Greenwood Lake offering gorgeous views in a spacious, stylish setting, with lake and beach access. Just a 5 minute drive to village restaurants and shops, 10 minutes to Tuxedo, and 15 minutes to Warwick, this is the perfect setting for a relaxed and fun getaway no matter what your plans. You'll never want to leave, but you'll always remember you stayed! Permit #: 21-07657 A

Jun. 4 – 11

$585 CAD per night

Guest favourite

Cabin in New Fairfield

4.98 out of 5 average rating, 257 reviews

The Little Lake Cabin— hot tub, fire pit, & kayaks

Named one of the best Airbnbs in CT by Business Insider, The Little Lake Cabin is the perfect place to soak in the magic of nature by relaxing, hiking, and enjoying the lake. The cabin is a place to slow down and reconnect. Spend your days on the lake, exploring nearby towns, wineries & antique shops & your nights in the hot tub, by the fire pit roasting s'mores and gazing up at the stars. Find us on IG @thelittlecabins

Aug. 25 – Sep. 1

$693 CAD per night

Vacation rentals for every style

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Popular amenities for Philipstown kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Guest favourite

Home in New Paltz

4.94 out of 5 average rating, 172 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Mar. 27 – Apr. 3

$470 CAD per night

Guest favourite

Home in Greenwood Lake

4.95 out of 5 average rating, 119 reviews

Latitude lake house with dock & lake access #31943

May 11 – 18

$563 CAD per night

Guest favourite

Home in Brookfield

4.98 out of 5 average rating, 121 reviews

Stay at Old Dorset Farm & create lifelong memories

Oct. 2 – 9

$603 CAD per night

Guest favourite

Home in Saugerties

4.95 out of 5 average rating, 103 reviews

Waterfront Three bedroom in Saugerties w/ Hot Tub

Sep. 25 – Oct. 2

$609 CAD per night

Guest favourite

Home in Monticello

4.91 out of 5 average rating, 101 reviews

Catskills Lakefront Haven w/ Hot Tub & Game Room

Nov. 15 – 22

$890 CAD per night

Home in Rhinebeck

4.84 out of 5 average rating, 238 reviews

Private Lakefront Bungalow

Jun. 10 – 17

$643 CAD per night

Home in New Paltz

4.89 out of 5 average rating, 126 reviews

Waterfront Renovated Hudson Valley House & Barn

Sep. 6 – 13

$1,508 CAD per night

Guest favourite

Home in Nyack

4.85 out of 5 average rating, 122 reviews

Beautiful & Fun Waterfront Duplex on the Hudson

Aug. 30 – Sep. 6

$606 CAD per night

Cottage rentals with a kayak

Guest favourite

Cottage in Highland Lakes

4.97 out of 5 average rating, 267 reviews

The Mountaintop Lakehouse that Time Forgot.

Nov. 19 – 26

$628 CAD per night

Guest favourite

Cottage in Kingston

4.81 out of 5 average rating, 146 reviews

Cottage w/ Deck @woodstockwellnessplace

Jun. 27 – Jul. 4

$215 CAD per night

Guest favourite

Cottage in Ulster Park

4.9 out of 5 average rating, 168 reviews

Romantic House on a Magical Lake

Jul. 18 – 25

$573 CAD per night

Guest favourite

Cottage in Red Hook

4.92 out of 5 average rating, 324 reviews

Goose Landing Cottage by the lake with NEW Hot Tub

Jul. 22 – 29

$390 CAD per night

Guest favourite

Cottage in Ancram

4.99 out of 5 average rating, 165 reviews

New Earlier Arrival/Later Departure

May 9 – 16

$467 CAD per night

Cottage in Putnam Valley

4.93 out of 5 average rating, 41 reviews

Charming Lake House 1 hour from NYC

Oct. 1 – 8

$592 CAD per night

Guest favourite

Cottage in Pawling

5.0 out of 5 average rating, 62 reviews

Twin Lakes Designer A-frame Stone Cottage

Apr. 12 – 19

$537 CAD per night

Guest favourite

Cottage in Newburgh

4.98 out of 5 average rating, 48 reviews

Lakefront Getaway 1 Hr from NYC

Jun. 5 – 12

$371 CAD per night

Cabin rentals with a kayak

Guest favourite

Cabin in Ferndale

4.93 out of 5 average rating, 156 reviews

Charming Catskills Lakefront Home—2 hrs from NYC!

Sep. 6 – 13

$454 CAD per night

Guest favourite

Cabin in Sussex

4.95 out of 5 average rating, 198 reviews

Lake Glenwood - Cozy Cabin Spectacular Lake Views

Dec. 20 – 27

$398 CAD per night

Guest favourite

Cabin in Kerhonkson

4.99 out of 5 average rating, 106 reviews

Modern Chalet w/ Firepit, BBQ, Fast Wi-Fi, Dogs Ok

Dec. 15 – 22

$584 CAD per night

Guest favourite

Cabin in Cochecton

5.0 out of 5 average rating, 119 reviews

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

Feb. 11 – 18

$352 CAD per night

Cabin in Smallwood

4.88 out of 5 average rating, 150 reviews

Lake Front Catskills Lodge

Nov. 6 – 13

$641 CAD per night

Guest favourite

Cabin in Saugerties

4.86 out of 5 average rating, 162 reviews

Private Woodstock Getaway w Hot Tub

Jun. 7 – 14

$868 CAD per night

Guest favourite

Cabin in Forestburg

4.82 out of 5 average rating, 251 reviews

Romantic Log Cabin in the Woods

Jul. 21 – 28

$313 CAD per night

Guest favourite

Cabin in Greenwood Lake

5.0 out of 5 average rating, 29 reviews

Modern Nordic Designed Cabin

Jul. 22 – 29

$466 CAD per night

Quick stats about vacation rentals with a kayak in Philipstown

Total rentals
20 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
$68 CAD before taxes and fees

Destinations to explore