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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Catskill

4.96 out of 5 average rating, 135 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access. We provide kayaks, SUP & complimentary tours of the Hudson by boat! Enjoy your private sauna & steam shower indoors and hot tub on lower deck - all for your exclusive use. Fish right off the property. Enjoy dinner in the Gazebo suspended over the Hudson. The area serves up plenty-Saugerties, Woodstock, Hudson, Hunter, Catskill. Honestly you'll not want to leave.

Sep 21 – 28

G$108,355 GYD per night

Guest favorite

Castle in East Stroudsburg

4.99 out of 5 average rating, 284 reviews

Pocono Castle w/ Private Pond, Boat, Sauna,Hot Tub

No need to go to England to enjoy Castle life. We invite you to come and relax in this 2300 square-foot Castle home. It features four bedrooms, two full baths in a lovely Pocono setting.Enjoy the wildlife while relaxing in the outdoor hot tub or rejuvenate in Cedar Sauna. Indoor and outdoor games for all ages. Everyone will enjoy role-playing King & Queen, when dressing up in the costumes we provide. There is a 1 acre private pond if you would like to try your hand at catching your Golden Fish!

Sep 30 – Oct 7

G$102,718 GYD per night

Guest favorite

Bungalow in Margaretville

4.97 out of 5 average rating, 229 reviews

The Porch Upstate Super clean

Halcottsville is a tiny hamlet In the heart of the Catskills .The porch is a compound with an old general store built in 1890 which is available for rent .We also have a restored barn , gardens and Apple orchard . The Bungalow is super private and still right on Main Street in Halcottsville. We will definitely will share our veggies and fruit with you . We have 3 sheep , 10 chickens and 5 barn cats .Halcottsville has its own post office ,voluntary fire department and a beautiful Lake.

Mar 12 – 19

G$29,706 GYD per night

Superhost

Cottage in Putnam Valley

4.9 out of 5 average rating, 215 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.

Apr 23 – 30

G$82,239 GYD per night

Guest favorite

Home in Putnam Valley

4.96 out of 5 average rating, 101 reviews

Lake Cottage Near Sleepy Hollow, Westpoint & NYC

Escape to this private lakeside cottage. Just 1h drive from NYC near lots of skiing: 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 The cottage can accommodate up to 10 guests and is family-friendly. Pets are welcome! WiFi is extremely fast and we have free electric car charging.

Jul 29 – Aug 5

G$158,147 GYD per night

Guest favorite

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 17 – 24

G$110,386 GYD per night

Guest favorite

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.

Jun 7 – 14

G$34,365 GYD per night

Guest favorite

Home in Greenwood Lake

4.95 out of 5 average rating, 193 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).

Sep 10 – 17

G$80,907 GYD per night

Guest favorite

Cabin in West Milford

4.98 out of 5 average rating, 111 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!

Sep 5 – 12

G$80,866 GYD per night

Guest favorite

Guesthouse in Gardiner

4.99 out of 5 average rating, 137 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.

Jun 12 – 19

G$43,257 GYD per night

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 311 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.

Apr 20 – 27

G$92,408 GYD per night

Guest favorite

Cabin in New Fairfield

4.98 out of 5 average rating, 258 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

Oct 24 – 31

G$79,906 GYD per night