Vacation rentals with a kayak in Hudson Valley

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Top-rated kayak rentals in Hudson Valley

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Guest favorite

A clear lake displays calm waters reflecting the surrounding greenery and mountains. Smooth stones line the water's edge, while trees provide a natural frame. A lakeside home is visible in the background, integrating seamlessly with the tranquil landscape.

Home in Chichester

4.97 out of 5 average rating, 159 reviews

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

Wake up to stunning mountain views and enjoy a SWIM in your OWN PRIVATE LAKE (only you!) sparkling clear lake surrounded by 5 secluded ac. of the stunning Catskill Mountains . Lie out on the swim dock, row the boat, enjoy coffee or grill on the wrap-around deck, cook in the gourmet kitchen, or simply relax by the fire (wood-burning fireplace inside as well as a lakeside FIREPIT). Minutes to swim holes, hiking, breweries & the town of Phoenicia. You need never leave! This is the ULTIMATE getaway.

Guest favorite

A spacious living area features two modern armchairs with orange accent pillows facing a large picture window. The serene view of the wooded area surrounding the private pond is visible, inviting natural light into the space. A low coffee table occupies the center, complemented by a soft sofa nearby.

Cottage in Saugerties

4.98 out of 5 average rating, 145 reviews

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

Guest favorite

The lakefront cabin is framed by lush greenery, with a blue exterior and multiple large windows reflecting onto the calm water. A wooden dock extends toward a turquoise kayak, surrounded by tall trees, creating a serene and inviting atmosphere.

Cabin in Ferndale

4.93 out of 5 average rating, 233 reviews

Charming Catskills Lakefront Home—2 hrs from NYC!

This beautiful lakefront cabin is located at the end of a peaceful road adorned with tire swings and wildflowers. It is situated in a private community on a SMALL 3 acre lake, offering the perfect setting to enjoy morning coffee on the dock, taking refreshing afternoon swims in the lake, going for evening kayaking rides, and stargazing. You can unwind in our hammock nestled amidst the ferns next to a tranquil stream. We offer 2 kayaks and 1 SUP for your enjoyment. Best of all, 2 hrs from NYC.

Top guest favorite

Four single kayaks and two stand-up paddleboards are situated on green grass, positioned near the water's edge. Two kayaks are hanging vertically on a wooden wall, while the others are laid out on the ground. The tranquil lake is in the background, framed by trees.

Cottage in Valatie

4.99 out of 5 average rating, 146 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the 8 miles of shoreline -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Top guest favorite

Place to stay in Remsen

5 out of 5 average rating, 209 reviews

ADIRONDACK LUXURY VILLA WITH HOTUB (NEW BUILD)

This brand-new luxurious property features floor to ceiling Marvin windows with with built-in hot tub and outdoor propane fireplace overlooking the glorious lake and mountain scenery! The all-white modern interior boasts high-end appliances and fixtures making your stay a true luxury escape. High end ‘TheCompanyStore’ bedding! Gourmet kitchen with 6 burner Zline gas stove, convection oven, built in fridge/freezer drawers and an Insta Hot water faucet for tea lovers. Smart auto flush toilet!

Top guest favorite

The cabin is illuminated at dusk, situated on a hillside overlooking a gently flowing river. Leafless trees frame the scene, and scattered leaves cover the ground. The water reflects the soft glow from the cabin, creating a serene atmosphere amid nature.

Cabin in Red Hook

4.97 out of 5 average rating, 101 reviews

Secluded luxury: modern riverfront fishing cabin

Far from the road, this tranquil and unique modern cabin overlooking state stocked fly fishing and tubing river is under 2 hours from NYC. Sited on a 120 acre property, the towns of Red Hook, Rhinebeck, Hudson and Kingston are all between 10 and 30 mins away. On property hiking and tubing for fun. Our chickens mean you'll have fresh eggs on arrival. Radiant floors, swedish compost toilet, a tesla powerwall and 500 mbps internet make it easy to get away from it all while staying in touch.

Top guest favorite

The exterior of the rustic lake house is highlighted by a vibrant blue-green facade and a bold red door. A stone chimney extends upward, surrounded by colorful autumn foliage. A pathway leads from the lawn to the lake's edge, offering a peaceful view of the water.

Cabin in Summit

4.99 out of 5 average rating, 110 reviews

Little Green Lake House

Owned and styled by an artist couple with the dream of providing a space for others to escape, reflect & feel reinvigorated by nature, this beautiful rustic lake house is nestled right on the bank of Summit Lake, deep in the Catskill Mountains. This thoughtfully renovated 1940s cabin is perfect for couples looking for a romantic weekend getaway, small families needing a relaxing break, writers & artists seeking inspiration, or really just anyone looking for a quiet & peaceful sanctuary.

Guest favorite

A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.

Home in Catskill

4.94 out of 5 average rating, 209 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access year round. We provide kayaks & stand up paddle board. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Fish right off the lawn. Enjoy brunch, dinner or high tea in the Gazebo suspended over the Hudson with a private chef (inquire about availability). Explore Hudson, Saugerties, Woodstock....honestly, you'll not want to leave.

Top guest favorite

Home in Saugerties

4.97 out of 5 average rating, 104 reviews

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Guest favorite

Cabin in Petersburgh

4.93 out of 5 average rating, 248 reviews

Cozy Retreat in the Trees

Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Guest favorite

A serene lakeside view showcases a vibrant green lawn framed by mature trees. Colorful kayaks and a paddleboard rest beside the water. A picturesque scene is enhanced by blooming pink azaleas, with the calm lake visible in the background.

Cottage in Pawling

4.99 out of 5 average rating, 134 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Top guest favorite

A serene lakeside view captures the setting sun, casting warm hues on the water's surface. The surrounding trees stand silhouetted against the vibrant sky, while soft clouds reflect on the calm lake, creating a peaceful atmosphere ideal for relaxation.

Cabin in Kingston

5 out of 5 average rating, 219 reviews

Lakeside Cottage: Boulder's Bluff

Come enjoy the serenity of our renovated lakeside cottage! Guests can enjoy their time relaxing fireside with panoramic views, hiking or biking 22 miles of trails running through our backyard, and let's not forget splashing around in the lake. We are sorry but we are unable to accommodate pets. Pack N Play available only when request ahead of time. Pack N Play sheets not provided.