Vacation rentals with a kayak in Long Island

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Top-rated kayak rentals in Long Island

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Top guest favorite

Cabin in Greenwood Lake

4.99 out of 5 average rating, 102 reviews

Modern Nordic Designed Cabin

Newly designed Modern Nordic Cabin. Escape to the tranquility of the mountains and lakes. The Nordic cabin is modern with high-end finishes throughout. The open concept living area features a fireplace, waterfall shower, vaulted ceilings, and large windows that offer stunning views of the surrounding forest and lake. Getting to and from NYC is easy. There is a bus stop down the street and a train station 15 minutes away. Perfect for a convenient getaway from the city Warwick town Permit 33274

Superhost

A shoreline view features soft sand bordered by water, with a green kayak resting beside a blue kayak. A tall tree stands nearby, and an American flag is seen waving in the breeze. The serene lake reflects the surrounding landscape.

Home in Greenwood Lake

4.87 out of 5 average rating, 165 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!

Top guest favorite

Home in Putnam Valley

4.99 out of 5 average rating, 127 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

Top guest favorite

A charming lakeside home with a red metal roof sits on a wooden deck overlooking the water. Surrounding landscaping features a serene pond, rocks, and green shrubs, creating a peaceful atmosphere. The setting sun casts a warm glow on the tranquil scene.

Home in Greenwood Lake

4.98 out of 5 average rating, 175 reviews

Fall Foliage! Apple Pick, Firepit, Kayak Ren Faire

Fall is the BEST time to visit! Enjoy the beautiful weather and views of the lake and changing leaves at this peaceful boho 3BR home in Greenwood Lake! This tranquil hideaway is minutes from all fall activities! Experience apple & pumpkin picking, nearby wineries, breweries, restaurants, hiking, Ren Faire & more! You'll love relaxing on the huge wrap-around deck, by the firepit, in the cozy living room, & utilizing the well-equipped kitchen. Your lakeside escape awaits!! ~ 1 hour from NYC

Guest favorite

Cottage in Monroe

4.98 out of 5 average rating, 176 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🐕

Top guest favorite

A wooden dock extends over calm waters, featuring a canoe and two stand-up paddleboards tied up. Lush trees line the opposite shore, reflecting in the water under a cloudy sky.

Cottage in South Salem

5 out of 5 average rating, 120 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.

Top guest favorite

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

4.99 out of 5 average rating, 107 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Top guest favorite

An aerial view captures the coastal neighborhood, with a sandy beach and clear blue water. The vibrant homes line the shore, featuring varied architectural styles. Lush greenery borders the area, enhancing the sense of tranquility and charm typical of beachside living.

Home in Milford

5 out of 5 average rating, 115 reviews

Steps2Beach, Fish Pond, Tropical Backyard Oasis!

🌴Steps from Walnut Beach, Silver Sands, dining, shops & more, this guest-favorite escape offers a tropical backyard oasis with a cascading fish pond, multiple lounges, & a seasonal palm tree. Explore the scenic coastline, build sandcastles, or enjoy a day of kite flying. Inside, relax in luxury with a gourmet kitchen, elegant furnishings, & modern amenities. Just 90 minutes from NYC & 15 from New Haven, it’s the perfect retreat for beach days, nature adventures, & coastal charm!

Superhost

The exterior features a charming facade with wooden shingles and a welcoming front porch. Two vibrant blue doors highlight the entrance, surrounded by blooming flower pots and neatly arranged greenery. White columns support the porch roof, enhancing the spacious feel of the entryway.

Home in Port Jefferson

4.89 out of 5 average rating, 161 reviews

Harborfront Star

Hang up your car keys and your worries and come visit this beautiful, stylish, coastal gem. Everything that Port Jefferson Village has to offer -- the marina, Harborfront Park, restaurants, clubs, shops, galleries, skating rink, green market, Danfords -- is all within easy walking distance. So come enjoy being in the middle of the action -- and the cool breezes off Long Island Sound -- at the Harborfront Star. We are dog friendly and have a pet fee of $65 per dog (max of 3 dogs).

Guest favorite

Double doors open to reveal a private balcony with views of the marina and Quinnipiac River. A small dining table is positioned near the doors, while comfortable seating is visible outside, framed by greenery. Natural light fills the space, creating a bright and airy atmosphere.

Loft in New Haven

4.88 out of 5 average rating, 105 reviews

Cozy Riverside Loft Getaway | New Haven

Escape to this charming Fall Foliage Loft on the Quinnipiac River! With a smart TV, full kitchen, bath, and pull-out sofa, it’s a perfect waterfront retreat. Enjoy autumn sunsets from your private balcony or stroll the colorful marina. Just off I-91, minutes from New Haven’s pizza scene and Lighthouse Point Park. On-site, savor oysters & cocktails at Fair Haven Oyster Co. Rent a kayak or e-boat, or book a charter to explore the river & Sound. Rest, relax, adventure & ENJOY 🍁🔥🍕

Superhost

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

4.85 out of 5 average rating, 112 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are closed and will open Memorial Day Weekend (late May 2026).

Superhost

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

Home in Mastic

4.86 out of 5 average rating, 125 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate