Holiday rentals with a kayak in Westchester County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Westchester County

Guests agree: these rentals with 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, 55 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.

15–22 Oct

€ 470 per night

Home in Rye

4.67 out of 5 average rating, 6 reviews

Bike to Beach Walk to Town & Train + Housekeeper

Experience our center hall colonial home, embraced by hydrangeas and old oak trees on private grounds, nestled in a secluded prime location. The neighborhood is safe for kids, with no traffic, making it ideal for families. Just a 5-minute walk from town. You can also easily access the beach and pools with a short bike ride. We're usually fully booked for long stays, so be sure to reach out early. Enjoy weekly housekeeping, allowing you to focus on making the most of your family holiday together.

21–28 Aug

€ 729 per night

Guest favourite

Home in Putnam Valley

5.0 out of 5 average rating, 38 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

22–29 Jun

€ 426 per night

Home in Mamaroneck

4.8 out of 5 average rating, 5 reviews

Charming cottage on the river ( bottom 2 floors)

Take it easy at this unique and tranquil getaway, 35 minutes from Midtown Manhattan. Walking distance to harbor, small beach, shopping area, restaurant row and the train to Manhattan. We have a lovely indoor/outdoor cat that needs minimum care. We have a romantic garden with lounge chairs overlooking the river. Where you can hear the calming and rippling sound of the stream. We also have a kayak you can launch straight from the backyard. This is a very safe area in sought after Westchester.

13–20 Oct

€ 226 per night

Guest favourite

Guest suite in Putnam Valley

4.91 out of 5 average rating, 33 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.

13–20 Mar

€ 103 per night

Guest favourite

Home in Putnam Valley

4.97 out of 5 average rating, 98 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.

24–31 Oct

€ 496 per night

Guest favourite

Cottage in South Salem

5.0 out of 5 average rating, 76 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-Yoga,Canoe, Bocce, Cornhole, Swim, Hike, Grill etc

9–16 Jun

€ 297 per night

Guest favourite

Home in South Salem

5.0 out of 5 average rating, 7 reviews

Spacious Lake Home for Peace and Relaxation

Unwind at our lakefront retreat, just an hour from NYC. The perfect blend of relaxation and recreation. During warmer months, enjoy lake Waccabuc, our swim platform, kayak, canoe, and SUPs. Lovely evenings by the fire pit, stargazing far from the city lights and fantastic hiking trails year round. The private road is perfect for kids and dogs . With room for 12 guests, our home is ideal for families or getaways with friends. Book now and savor the tranquility of this lakeside gem.

1–8 Nov

€ 758 per night

Superhost

Boat in West Haverstraw

4.8 out of 5 average rating, 6 reviews

Yacht at Dock - On the Waterfront!

Note: Please understand that the boat is on the river and on the move. Text to check current location and availability BEFORE you try to book. Great locations on the Hudson River with a great view of New York City in Summer months but definitely not in the hustle and bustle. Walk to restaurants and Statue of Liberty park. A quick ferry ride to Manhattan ($5). Currently the boat is upriver at Stoney Point NY. Fellow boaters preferred... and an adventure for land lubbers too.

6–13 Jun

€ 113 per night

Guest favourite

Home in Putnam Valley

5.0 out of 5 average rating, 38 reviews

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Kayak, Swim, Boat & Fish 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!

6–13 Feb

€ 491 per night

Guest favourite

Home in Nyack

4.85 out of 5 average rating, 122 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.

30 Aug – 6 Sep

€ 414 per night

Superhost

Home in Stamford

5.0 out of 5 average rating, 48 reviews

Waterview House Walking Distance from Cove Beach

This is a spacious 5 bedrooms luxury home with water views located walking distance to Cove beach/park, tennis /basketball courts, ice rink. The house is perfect for a large family or a corporate retreat. If this property is booked for the dates you selected, click on the profile to see our other amazing properties in Stamford. Travelers looking for better rates may book directly on our website: Miami Luxury Access . com

1–8 Dec

€ 869 per night