Vacation rentals with a kayak in Philipstown

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Top-rated kayak rentals in Philipstown

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Guest favorite

Home in Monroe

4.96 out of 5 average rating, 111 reviews

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

Kitchen & Basement Newly Finished!! Enjoy your very own LAKEFRONT WONDERLAND with a trove of amenities and space to WFH with fast internet! A perfectly manicured landscape with a Goldilocks-sized pool. The lawn leads to your very own private dock and brick patio, containing a fire-pit. Swim to your heart's content in the pool or in the lake. Soak in the hot tub. Paddle in our canoe or kayak and try snagging some brown trout. Plenty of room for a large extended family or a group of friends.

Guest favorite

Home in Greenwood Lake

4.98 out of 5 average rating, 100 reviews

Your lakefront castle awaits you …

Imagine a castle on a lake. Welcome to Castlebrook, a luxurious Lakefront home on Greenwood Lake, NY. This exquisitely appointed home has sweeping vistas of the lake yet is private enough for a relaxing getaway. 3 large bedrooms, 3 full baths, boat slip, jet ski dock, outdoor grill and firepit, meticulously manicured grounds await you just an hour from NYC, 15 minutes from Tuxedo train, 30 minutes from Legoland. Spacious entertaining areas, all with sweeping views of the lake. True luxury.

Guest favorite

Home in Rock Hill

4.9 out of 5 average rating, 119 reviews

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!

Guest favorite

Cottage in Highland Lakes

4.97 out of 5 average rating, 301 reviews

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

Guest favorite

Cottage in Putnam Valley

4.88 out of 5 average rating, 250 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.

Guest favorite

Place to stay in Hopatcong

4.94 out of 5 average rating, 182 reviews

Lake Sports Home & Super water sports!

Luxury water front suite, 40 ft. deck, 13 floor to ceiling windows, king bed, bath, BIG TV, LED fireplace, Hot Tub, dock, . Capacity 2 guests but 2nd bedroom + bath or 2 single rolling beds are avail. for additional charge -so capacity up to 6. Other: kitchen appliances, firepit, BBQ grill, 3 hammocks, dining table, and deck chairs. Electric mountain bikes , quality kayaks, rafts incl. Extras: we need to talk about: Boat, electric surfboards, jet skis, hydrofoils, Permit 2024-13

Guest favorite

Cottage in Monroe

4.99 out of 5 average rating, 145 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🐕

Guest favorite

Home in Greenwood Lake

4.96 out of 5 average rating, 233 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).

Guest favorite

Home in Greenwood Lake

4.98 out of 5 average rating, 107 reviews

Peak Fall Foliage! Hike, Apple Pick, Lake View!

Escape to this cozy, relaxing, 3BR home in Greenwood Lake! Enjoy amazing views of the lake & mountains across the way. You'll love the deck and firepit to roast marshmallows, drink hot cocoa, and hang. Inside has plenty of games to enjoy around the warm wood-burning stove. Explore nearby Nearby winter hiking, skiing, wineries, breweries, restaurants, & more! Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing. 1 hr from NYC. Warwick STR Permit # 32574

Guest favorite

Cabin in Sherman

4.97 out of 5 average rating, 344 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.

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 103 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.

Guest favorite

Cottage in Putnam Valley

4.95 out of 5 average rating, 135 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