Holiday rentals with a kayak in Westchester County

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Westchester County

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

1 of 1 pages1 / 1

Top Guest favourite

Two lounge chairs are positioned on a wooden deck overlooking a serene lake, framed by lush greenery and rolling hills in the background. The calm water reflects the surrounding nature, creating a peaceful outdoor retreat.

Home in Waccabuc

4.99 out of 5 average rating, 68 reviews

Modern Lakefront Home in Hudson Valley

Welcome to your modern lake house! This beautiful home sits on 4 secluded acres on a private lake with a private beach. It is perfect for a week-end get-away or a long-term rental. Close to Ridgefield, Ward Pound Ridge Reservation, and Katonah. Lots of hiking trails and nature preserves nearby! The house is a quick 1-hr drive from New York City. Only 25 minutes to ski and Thunder ridge or ice skate from the private dock. Waccabuc lake is also an excellent spot for ice and fresh water fishing.

LocationValueGetting around

Superhost

A large willow tree extends gracefully over the calm waters of Lake Waccabuc, framing a peaceful view of the surrounding autumn foliage. Stone patio chairs offer a place to relax, while a small fire pit rests on the grassy shore, creating an inviting outdoor space.

Cottage in South Salem

4.86 out of 5 average rating, 49 reviews

Charming Lake Front Cottage - Paradise Rest Home

Charming and Quiet Lake Front Cottage on Lake Waccabuc, NY. Renovated upstairs and living room 2023 Looking for a full time place to live or just a weekend break? Need a quiet spot with amazing views, incredible lake access, a cozy fireplace, wifi and all the basics covered? Perfect for 2-4 adults or a family of 3-6 The house is stocked with Nespresso coffee, condiments, cooking spices and supplies and all of it is meant to BE USED BY OUR GUESTS! A true livable vacation spot No cleaning needed

Outdoor spacesLocationFamily

Top Guest favourite

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

Home in Putnam Valley

4.99 out of 5 average rating, 185 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

LocationOutdoor spacesBarbecue

Guest favourite

The historic waterfront home is shown with a light yellow exterior and an A-frame roof. A welcoming porch with seating faces the river, framed by trees that add touches of color. The serene Hudson River is visible in the background under a clear blue sky.

Home in Nyack

4.86 out of 5 average rating, 160 reviews

Beautiful & Fun Waterfront Duplex on the Hudson

Enjoy a getaway to this charming historic waterfront home. Sip a glass of wine, a cup of Joe, or a refreshing cool drink from the 36 ft deck overlooking the Hudson River and Mario Cuomo Bridge beautifully lit up each evening. **PLEASE read everything in the description of "The Space" and "Other Things to Note" before booking. Thank you! Check out my "GUIDEBOOK" for my favorite picks including entertainment, shopping, eateries, and more. Non shedding pets welcome with additional fee $150.

LocationOutdoor spacesWalkability

Top Guest favourite

Cottage in South Salem

5 out of 5 average rating, 136 reviews

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

LocationValueSleep quality

Superhost

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

4.94 out of 5 average rating, 136 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.

LocationOutdoor spacesCondition

Superhost

Home in North Salem

5 out of 5 average rating, 6 reviews

Pet Frndly Lake House w/Fireplace & Fire Pit W/D

Relax with the whole family at this peaceful place to stay. You’ll enjoy a yard, parking for 2 cars, fire pit, and a peaceful neighborhood where you can enjoy day walks. Your pets are welcome during your stay- we will ask about the breed and size- pets are not allowed on the beds or couch. You also have access to the lake just steps from this home. Train station is just 10 min away. Enjoy the farms, restaurants and scenery of North Salem, a place where your whole family can enjoy!

LocationAccuracyComfort

Superhost

Apartment in Yonkers

5 out of 5 average rating, 3 reviews

Hudson River Views | Private Balcony+ 2 Gyms

Wake up to stunning Hudson River views from this thoughtfully designed 1 bedroom apartment with a private balcony. Just a 10 minute walk to Metro North with Grand Central only 25 to 30 minutes away. Enjoy two fitness centers, a resort style pool, rooftop lounges, fast WiFi, and a fully equipped kitchen. Perfect for business trips, weekend getaways, or exploring NYC without staying in Manhattan. Staying for the FIFA Club World Cup Final? MetLife Stadium is only 30 minutes away.

QuietHospitalityRiver

Guest favourite

A serene waterfront view features a tranquil lake at sunset, with vibrant shades of orange and pink reflecting in the water. Silhouetted trees frame the scene, while a kayak rests on a wooden dock, enhancing the natural beauty of the setting.

Home in Haverstraw

4.94 out of 5 average rating, 78 reviews

Beachfront Home on the Hudson w/ Amazing Views!

Just 45 minutes from NYC, this art-filled, beachfront home on the Hudson is a hidden gem. Enjoy peace + quiet + privacy. Relax on the treehouse - like deck + enjoy the amazing view. If you love nature, you can walk or hike + then take a hot tub + watch the boats go by. Or launch a kayak from our beach (use of kayaks 6/1 - 8/31). Kick off your shoes + make yourself at home at this hide-away on Haverstraw Bay! Not sure? Please read our past guests’ reviews!

Outdoor spacesLocationBarbecue

Top Guest favourite

A spacious room features warm hardwood floors and large windows allowing natural light. A king size bed is adorned with light bedding and soft pillows. A comfortable sofa can be seen in the background, alongside a wooden coffee table and plants, fostering a relaxed atmosphere.

Apartment in Stamford

4.94 out of 5 average rating, 70 reviews

Spacious. Water Views & Access. Steps to Beach.

Spacious apartment with King Size Bed. Direct access to Cove Pond & Long Island Sound. Easy access to downtown Stamford, Stamford Train Station & Manhattan. A few steps away from Cove Island Beach & Park. Apartment features high ceilings, central heating & cooling, brand new washer & dryer, hardwood floors, formal dining room and 60" HDTV with Amazon Fire TV. Guests have complimentary access to YouTube TV (comparable to cable), Peacock, & Prime Video.

LocationOutdoor spacesWi-Fi

Top Guest favourite

A cozy living area features high ceilings and large windows, allowing natural light to fill the space. A gas fireplace adds warmth, complemented by plush seating arrangements. A stylish rug lies beneath the furniture, and access to the adjacent rooms is visible.

Home in South Salem

5 out of 5 average rating, 44 reviews

Casa Luna Lake House

Enjoy a quiet, peaceful getaway at Casa Luna! Sits on a property with two separate cottages. Across the street from the lake and with numerous hiking trails and parks in the area. Enjoy a cozy fire at the cabin with the outdoor firepit. Only 4 miles to Le Chateau wedding venue. An easy 10-minute drive to Ridgefield, CT for groceries, tons of restaurants, and other activities. Close to numerous Metro North train stations for easy access to NYC.

LocationOutdoor spacesKitchen

Top Guest favourite

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

4.97 out of 5 average rating, 242 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

LocationValueWi-Fi