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.

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Guest favourite

Home in Waccabuc

4.98 out of 5 average rating, 57 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.

Superhost

Cottage in South Salem

4.84 out of 5 average rating, 45 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

Top Guest favourite

Home in Putnam Valley

4.99 out of 5 average rating, 123 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

Superhost

Home in North Salem

5 out of 5 average rating, 4 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, BBQ grill 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!

Guest favourite

Guest suite in Putnam Valley

4.94 out of 5 average rating, 69 reviews

Peaceful lake and woodland retreat

Welcome to beautiful Lake Peekskill. This self-contained guest suite is situated in the entire lower level of a private house down several steps, featuring its own private door access, as well as parking on site. Guests can access the grounds of the house including areas to sit, a native wildflower pasture, and a woodland with wildlife including deer, foxes, and birds. Lake access is a 15-min walk away (or a 3-min drive) to a beach area where guests can swim, fish, and make use of two kayaks.

Guest favourite

Home in Nyack

4.86 out of 5 average rating, 145 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.

Top Guest favourite

Cottage in South Salem

5 out of 5 average rating, 116 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.

Guest favourite

Home in Putnam Valley

4.98 out of 5 average rating, 80 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.

Superhost

Apartment in Stamford

4.93 out of 5 average rating, 46 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.

Guest favourite

Home in Putnam Valley

4.95 out of 5 average rating, 96 reviews

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Water activities on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!

Top Guest favourite

Home in South Salem

5 out of 5 average rating, 23 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.

Guest favourite

Cottage in Putnam Valley

4.96 out of 5 average rating, 179 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