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 fire pit made of stacked logs is in the foreground, with bright flames dancing above. In the background, a serene lake is flanked by lush trees, reflecting the surrounding mountains bathed in early morning light.

Home in Chichester

4.98 out of 5 average rating, 164 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.

Top guest favorite

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, 129 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

Two wooden Adirondack chairs are positioned on a dock overlooking a calm lake at sunset. A kayak with an oar rests nearby, and the water reflects vibrant hues of orange and pink, bordered by trees in the background.

Cabin in Ferndale

4.93 out of 5 average rating, 240 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

The exterior of a modern house is illuminated by warm lights during twilight. Large windows and multiple balconies showcase the architecture, surrounded by trees and natural greenery. A gravel path leads towards the house, enhancing the inviting ambiance of the mountain setting.

Home in Mount Tremper

4.96 out of 5 average rating, 110 reviews

Chef's kitchen, seclusion, and breathtaking views

This is an incredible house for groups, spacious, flooded with light, andd spectacular views from almost every room. The main level is a massive open living room/ chef's kitchen/ dining/ fireplace on one level and a sweeping sunny deck. The home features 3 main bedrooms with ensuites, plus 2 other big bedrooms, a total of 5 bathrooms, and a yoga room with views. The perfect, central Catskill location gives you access to restaurants, farm stands, hiking, skiing, Phoenicia, Woodstock, and more!

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, 115 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, 218 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

A well-groomed dog is seated by the waterfront on a wooden deck surrounded by autumn leaves. Two patio chairs and a small table are positioned nearby, creating a peaceful setting that invites relaxation by the creek.

Home in Saugerties

4.97 out of 5 average rating, 111 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.

Top guest favorite

A wooden dock extends into the calm waters of the Esopus Creek, surrounded by lush greenery. The tranquil surface of the water reflects the surrounding trees, creating a serene atmosphere. Smooth stone steps lead down to the water's edge, enhancing accessibility.

Home in Saugerties

4.96 out of 5 average rating, 310 reviews

Creekside Cottage

Set on the beautiful Esopus Creek, this lovely 2 BR, 2 bath home is perfect for a get-away w/family, friends or a romantic or creative retreat. It's just a 15-20 minute drive to the quaint Village of Saugerties, Kingston, Woodstock & Rhinebeck. Sit & watch the river run by on the screened porch or on the deck down by the river's edge, bbq (4 burner gas stove), play board games, take a kayak or swim in the river. Kitchen w/full amenities. Pets are not allowed unless pre-approved.

Guest favorite

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

4.97 out of 5 average rating, 409 reviews

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Guest favorite

An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.

Cottage in Livingston

4.98 out of 5 average rating, 104 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

Guest favorite

The interior space features a high vaulted ceiling with skylights, allowing ample natural light. A stone fireplace serves as a focal point, complemented by a comfortable seating area. A wooden dining table and a kitchen island with a butcher block top are also present.

Cottage in Pawling

4.99 out of 5 average rating, 141 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 spacious deck is shown with lightly stained wooden flooring and several wooden chairs arranged in a circle. In the background, a large two-story home is visible, surrounded by greenery and trees under a clear blue sky.

Home in Averill Park

5 out of 5 average rating, 101 reviews

Lakefront escape w/ Breathtaking Bald Eagle Views

Wake up to bald eagles soaring past floor-to-ceiling windows in the lakefront great room. Relax by the fireplace or unwind in the cozy TV room. A spacious kitchen makes cooking easy. Upstairs: 4 bedrooms (2 king, 2 queen, all w/ desks) + 4 full baths (3 w/ showers, 1 w/ tub). Enjoy fast Wi-Fi, seasonal lake access, dock, and deck. Swim or kayak at your own risk (no guest boats at dock per insurance). Your lakeside getaway awaits!