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Vacation rentals with a kayak in Orange County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Orange County

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Home in Greenwood Lake

4.83 out of 5 average rating, 121 reviews

Aster Place

A beautiful and cozy home nestled in the Forest Hills section of Greenwood Lake, just over an hour outside of New York City. Boasting nearby activities in each season, including wineries, skiing and lake activities, this is a perfect year-round retreat. located 1/2 mile from our quiet community beach allows for a serene daily chill by the water. Town center is a short drive away, or 15 minutes from all that Warwick has to offer, you will enjoy this perfect setting for your lakeside getaway!

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.

Home in Greenwood Lake

4.98 out of 5 average rating, 101 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.

Cottage in Highland Lakes

4.97 out of 5 average rating, 303 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.

Home in Rock Hill

4.9 out of 5 average rating, 123 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!

Cabin in Sussex

4.95 out of 5 average rating, 220 reviews

Lake Glenwood - Cozy Cabin Spectacular Lake Views

Indulge in a truly breathtaking getaway. Nestled in a serene location with stunning lake views in Vernon Township, NJ. Close to Mountain Creek, Crystal Springs & Warwick, NY. Luxury & comfort, prepare to be pampered. Fully stocked chef's kitchen, themed bedrooms,"Ski Room & Canoe Room". Stone shower this cozy cabin boast carefully curated decor & beautiful lighting a soothing ambiance at this cottage dreamhouse. A chalet vibe to rejuvente as you bask in the warm glow of the stone fireplace.

Home in Monticello

4.93 out of 5 average rating, 123 reviews

Catskills Lakefront Haven w/ Hot Tub & Game Room

Indulge in the serenity of our lakefront haven, situated along 100ft of Sackett Lake's private shoreline. Here, year-round enjoyment is a promise - be it summer swimming, kayaking, or winter ice fishing and snowmobiling. Mere minutes away from Holiday Mountain, Casino, Waterpark, breweries, and Bethel Woods, our modern home boasts a vast deck and an 8-person hot tub. This is more than just a getaway; it's a sanctuary for creating unforgettable memories. Don't miss the chance to experience it!

Cottage in Vernon Township

4.88 out of 5 average rating, 149 reviews

Lakefront Home + Beach/Ski/Golf 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 paddle boards, all included. Permit: 220004 Must be 21+ to book.

Cottage in Monroe

4.99 out of 5 average rating, 146 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🐕

Home in Greenwood Lake

4.96 out of 5 average rating, 236 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).

Home in Greenwood Lake

4.98 out of 5 average rating, 110 reviews

Holiday season with 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

Cabin in Wantage

4.86 out of 5 average rating, 133 reviews

ECHO cabin - lakefront peaceful modern house

ECHO cabin is quiet waterfront property with your private access to the lake, amazing views, wood burning fireplace, outdoor grill and fire pit Only 60 miles from NYC 15 min drive from Mountain creek ski resort, waterpark and downhill biking 5 min drive from tiny Sussex airport for private planes and skydiving 5 min drive from Sussex town, local restaurants, diners and Arco supermarket 5min drive from free tennis courts Local hand pick fruit farms, horse ranch and alpaca farm

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Orange County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Vernon Township

5 out of 5 average rating, 55 reviews

Private Island + Lakefront Home

Home in Greenwood Lake

5 out of 5 average rating, 17 reviews

Casual Modern Lakefront/Gameroom/Greenwood Lake

Home in Cuddebackville

5 out of 5 average rating, 22 reviews

Riverfront Retreat | Hot Tub, Firepit & Pool Table

Home in West Milford

4.97 out of 5 average rating, 66 reviews

🛶 Lakefront Paradise with Your Own Private Beach🏖

Home in West Milford

5 out of 5 average rating, 31 reviews

Stunning Lakefront Dream Home!

Home in Greenwood Lake

5 out of 5 average rating, 14 reviews

7 ZEN Luxury Cabin in the Woods

Home in Greenwood Lake

4.91 out of 5 average rating, 54 reviews

Vintage Lake House Appalachian Trail &Skiing 33762

Home in Godeffroy

4.98 out of 5 average rating, 57 reviews

Lake House with Private Dock, Grill, and Fire Pit

Cottage rentals with a kayak

Cottage in Greenwood Lake

4.95 out of 5 average rating, 44 reviews

5 bedroom 7 beds Cottage Relax, Hike, Winery & Ski

Cottage in Newburgh

4.97 out of 5 average rating, 59 reviews

Lakefront Getaway 1 Hr from NYC

Cottage in Rock Hill

4.95 out of 5 average rating, 60 reviews

Lakefront Property in the Heart of the Catskills!

Cottage in Walden

4.72 out of 5 average rating, 43 reviews

Modern Cottage on Orange Lake w/ Fireplace

Cottage in Matamoras

4.96 out of 5 average rating, 26 reviews

Waterfront Cottage HOT TUB

Cabin rentals with a kayak

Cabin in Forestburg

4.83 out of 5 average rating, 261 reviews

Romantic Log Cabin in the Woods

Cabin in Greenwood Lake

4.98 out of 5 average rating, 61 reviews

Modern Nordic Designed Cabin

Cabin in Vernon Township

4.96 out of 5 average rating, 68 reviews

Perfect Getaway for Every Season! 1 hr from NYC

Cabin in Marlboro

5 out of 5 average rating, 7 reviews

Cascade-Cabin

Cabin in Vernon Township

4.5 out of 5 average rating, 10 reviews

Lakefront cabin w/modern decor

Cabin in Monroe

4.96 out of 5 average rating, 83 reviews

Modern - Secluded Lake Cabins- 35 miles from NYC

Destinations to explore