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Vacation rentals with a kayak in Columbia County

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Top-rated kayak rentals in Columbia County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.

4.95 out of 5 average rating, 148 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, kayaks, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

The exterior of the lakefront home showcases a vibrant blue facade, framed by well-maintained green lawns and leafy trees. A spacious deck is visible, along with multiple large windows that enhance the inviting appearance of the property.

Home in Valatie

5 out of 5 average rating, 121 reviews

Escape to Lakefront Leisure—Amazing views!

Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and relax on Lake Kinderhook!! Brand new 6 person hot tub. Relax and unwind while 45 jets massage your muscles, summer or winter! Ever sit in the steaming hot water while snow falls around you? Upgraded 400/100 internet for work/school! About 2 hrs from New York City!

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

Home in Great Barrington

4.96 out of 5 average rating, 170 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

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, 145 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.

A modern living space is featured with large windows allowing natural light to fill the room. Comfortable seating, including a plush sofa and stylish chairs, surrounds a wooden coffee table. A patterned area rug adds warmth to the sleek, tiled floor.

Home in Valatie

4.97 out of 5 average rating, 36 reviews

Majestic lake front house

Experience the ultimate retreat at our 2,100 sq ft 2 bedroom, 2.5 bathroom, modern lake front property. Enjoy swimming, fishing, free kayaking and paddle boarding on our Private Lake. Relax and unwind at our Outdoor Fire Pit or simply enjoy the picturesque view out of our floor to ceiling picture windows. Your Dream Family Reunion at our Secluded 26-acre Property awaits. We are also open to host a small, QUIET Wedding or similar event. There is no review yet, it is newly up for str.

A serene lake is bordered by lush greenery and the reflection of a rustic lake house. Vibrant red accents adorn the structure, providing a contrast to the surrounding nature. Kayaks and a dock are visible at the water's edge, inviting exploration.

Cabin in Climax

4.91 out of 5 average rating, 44 reviews

Catskills Lake Cabin on 100 Wooded Acres

Relax and refresh in this unique, newly renovated cabin on 100 wooded acres! Located minutes from the town of Coxsackie, the Hudson River and the Catskill Mountains, this historic cabin blends rustic charm and access to nature with comfort and convenience. High-speed WiFi and a fully stocked kitchen make this a perfect remote work destination. Ready to explore? Hike 3+ miles of on-site trails, swim or canoe in the lake, tour nearby breweries, orchards and antique stores or kayak the Hudson!

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, 207 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 spacious deck features sleek, dark chairs lined up for relaxation, with a table set conveniently for outdoor dining. The surrounding trees provide a natural backdrop, while expansive windows on the house offer views of the lakeside scenery.

4.97 out of 5 average rating, 30 reviews

Lakeside home with Private dock and more !

Sleepy Hollow Ny is a lakeside community in upstate Ny that hosts endless opportunities for fun and memories with your family and friends.A clean Newly renovated home, with private deck and dock are the heart of your stay . Space for everyone , with spa like bathrooms this space will give you a fresh start to each day of your vacation and end with a lakeside sunset around the beautiful outdoor table. Kayak , paddle board or just float around in between, either way you will feel relaxed.

A spacious lakefront home is nestled among tall trees, with a sloping green lawn leading to the deck. The house features a distinctive A-frame design with large windows, allowing natural light to fill the interior. Shadows from the surrounding trees enhance the serene outdoor setting.

Chalet in Athens

4.88 out of 5 average rating, 112 reviews

Waterfront Lake Home, close to Hunter & Windham

Located w/in the Sleepy Hollow Lake community, adjacent to The Hudson River, offering an unrivaled location to experience all that Hudson has to offer. The quaint community of Sleepy Hollow is 30 minutes from Hunter Mountain & Wyndham Mountain, and 20 minutes from Hudson. The community enjoys its own beach, boat ramp, tennis courts, bocce ball court, 2 swimming pools (seasonal), outdoor full-size basketball court, a baseball/softball field, volleyball court, and a golf driving range.

A tranquil outdoor scene showcases several wooden Adirondack chairs arranged around a fire pit, facing a calm body of water. The surrounding trees exhibit vibrant autumn colors, reflecting beautifully in the water, creating a serene natural atmosphere.

Cottage in Hudson

4.83 out of 5 average rating, 138 reviews

Kayak, pet a Highland cow, have dinner in Hudson!

Love nature? Enjoy your own entire home on the Stockport Creek with private kayak/boat launch to the Hudson River. Hiking and bike trails nearby. You are immersed in Columbia County’s rural beauty between the Berkshires and the Catskills with Hudson’s hopping food and art scene minutes away. OMI sculpture park, Olana, farm markets, and Warren Street are a short drive. Ski Hunter or Catamount. Cozy wood burning stove as well as outdoor fire pit. Ask about a farm visit!

A covered porch features comfortable seating with soft cushions, offering expansive views of the lake and surrounding trees during sunset. The warm light casts a golden hue, enhancing the serene outdoor space, while a small table sits in the center, inviting relaxation.

Home in Pine Plains

4.98 out of 5 average rating, 128 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great area for hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

An aerial view captures the lakefront cabin nestled among lush greenery, surrounded by expansive trees. The property features a private dock extending into the water, with neighboring cabins displaying varied architecture in the serene landscape.

Cabin in Athens

4.94 out of 5 average rating, 106 reviews

Charming Lakefront Cabin with Hot Tub

Thoughtfully updated lakefront cabin, north of the Catskill mountains, in the Hudson Valley. Located inside the private, family-friendly Sleepy Hollow Lake community with guest access to pools, beach, tennis courts, & basketball (May-Sep). A peaceful retreat - come watch the hummingbirds from the porch or have your morning coffee looking out upon the lake! The cabin faces west over the lake so it's a wonderful spot to watch the sun set!

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Columbia County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

4.95 out of 5 average rating, 58 reviews

A/C! Hot Tub, Movie Room, & Private Beach Access!

A tranquil scene showcases a modern farmhouse set against a lush green landscape. A swimming pond lies in the foreground, bordered by natural vegetation, while a wooden dock and a kayak are visible along the water's edge.

Home in Hillsdale

4.96 out of 5 average rating, 56 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

Top guest favorite

A cozy living area features a tufted blue sofa paired with a rocking chair and an ornate side table. Soft light filters through two windows, illuminating a central coffee table set on a patterned rug. Decorative elements include a plant, lamp, and framed artwork on the walls.

Home in Salisbury

5 out of 5 average rating, 50 reviews

Greystone at Twin Lakes

Top guest favorite

A wooden dock extends toward a tranquil lake, framed by a large tree. Various watercraft, including a bright orange kayak and several boards, are positioned along the shore, inviting exploration of the serene waters and scenic surroundings.

4.97 out of 5 average rating, 60 reviews

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View

A wooden dock extends over calm waters, surrounded by lush greenery. Two white Adirondack chairs are positioned for relaxing views, facing the serene lake. Tall reeds frame the scene, enhancing the natural setting under a partly cloudy sky.

4.96 out of 5 average rating, 24 reviews

Lakeside Haven

Top guest favorite

A spacious living area features a combination of comfortable seating, modern decor, and a large flat-screen television. Natural light fills the space through multiple windows, enhancing the open layout that connects to a dining area visible in the background.

5 out of 5 average rating, 20 reviews

Lake house with arcade games

Top guest favorite

Aerial view of the River Retreat showcasing the house surrounded by lush greenery and tall trees. The Hudson River flows gently in the background, and a fire pit area with seating is visible on the expansive lawn, inviting relaxation in a serene setting.

Home in Coxsackie

4.99 out of 5 average rating, 83 reviews

Hudson River Retreat- Spectacular Views

A wooden deck is lined with adirondack chairs and overlooks a serene lake. Flourishing trees provide a natural backdrop, while pink flowering shrubs add pops of color. A grill is positioned at the far end of the deck, inviting outdoor dining and relaxation.

4.93 out of 5 average rating, 30 reviews

Artsy lake house on an island

Cottage rentals with a kayak

Cottage in Copake

4.85 out of 5 average rating, 54 reviews

Lakefront Retreat on Robinson Pond

A cozy three-bedroom cottage is shown at night, with warm light emanating from the windows. A wooden deck is visible, featuring two rocking chairs. Subtle string lights are strung along the edge, enhancing the outdoor space's inviting appeal.

Cottage in Canaan

4.9 out of 5 average rating, 139 reviews

Plan your Berkshires by the lake

Top guest favorite

The sunroom features large windows that provide expansive views of the lake, allowing natural light to fill the space. A comfortable seating area includes a cozy chair and decorative pillows, complemented by a small table with plants. The wood-paneled walls add warmth to the environment.

Cottage in Livingston

4.99 out of 5 average rating, 93 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

A serene lakeside view is presented, featuring a calm water surface reflecting surrounding greenery. Three adirondack chairs are positioned on a stone patio, facing the lake. A sailboat with a red and white sail glides gently across the water, enhancing the tranquil atmosphere.

Cottage in Copake

4.86 out of 5 average rating, 44 reviews

Lake Front Cottage with Sun Soaked Terraces

A spacious deck overlooks the lake, featuring a glass dining table surrounded by yellow chairs. A lounge chair is positioned nearby. A bright yellow umbrella provides shade, and trees frame the scene, accentuating the sunset sky in the background.

Cottage in Craryville

4.81 out of 5 average rating, 132 reviews

Oriole Cottage@Copake Lake:Swim, Kayak, Canoe

A serene view of a lakeside cottage set against a backdrop of vibrant autumn foliage. The structure features a spacious deck and a screened gazebo, with a private dock extending into the calm waters. The scene captures the tranquil essence of the lakeside environment.

Cottage in Niverville

4.97 out of 5 average rating, 37 reviews

Huge Lakefront, Cozy Private Cottage in Upstate NY

The image captures a serene lakeside view of Juliette's Chalet, nestled among lush green trees. A wooden dock extends into the calm water, reflecting the surrounding foliage. The house is partially visible, showcasing its inviting outdoor space.

Cottage in Athens

4.51 out of 5 average rating, 67 reviews

Lakefront 4BR, 3 bath, Sauna, Fireplace, game room

An outdoor patio area is visible, featuring a blend of vibrant seating options including blue, yellow, and green chairs. The patio is complemented by a wooden deck and well-maintained grass, surrounded by lush greenery and trees, offering a peaceful setting for gatherings.

Cottage in Copake

4.89 out of 5 average rating, 72 reviews

Stunning Lakeside, Year-Round Berkshire Getaway

Cabin rentals with a kayak

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, 99 reviews

Secluded luxury: modern riverfront fishing cabin

The modern cabin exterior features a dark blue facade with a wooden front door and expansive deck. A hammock is gently hung on the upper level, surrounded by lush green trees. Firewood is neatly stacked near the entrance, enhancing the outdoor atmosphere.

Cabin in Hillsdale

4.98 out of 5 average rating, 47 reviews

Modern hilltop chalet-style cabin @ Copake Lake

The exterior of the Cosmos Cottage is shown, featuring a wooden deck with steps leading to the entrance. A picnic table is positioned on the wooden decking, surrounded by greenery and trees. The building's windows reflect the natural light under a clear blue sky.

Cabin in Austerlitz

The Cosmo Cottage

An aerial view reveals a serene, wooded setting surrounding a lakefront home. The property features a grassy area leading to the water's edge, with a sandy spot for relaxing. Canoes are visible at the waterfront, complementing the natural landscape.

Cabin in Athens

4.97 out of 5 average rating, 70 reviews

Lakefront | Mountains | Family | Peaceful | Ski

A cozy cabin is surrounded by trees, featuring a spacious wooden deck with an umbrella for shade. A star decoration is visible near the roof. The cabin has multiple windows, inviting natural light, and steps leading to the deck from the yard.

Cabin in Hillsdale

4.86 out of 5 average rating, 14 reviews

Cozy Yellow Cabin at the Lake

A rustic porch features a wooden rocking chair and hanging ferns, alongside a lantern and bird feeder. The surrounding greenery is visible through the railing, creating a peaceful outdoor setting.

Cabin in Athens

Cheerfull 3 bedroom cabin nestled in the woods

A spacious cabin features a mixture of wood siding and large glass windows, blending into the surrounding greenery. A deck is visible, furnished with seating and a fire pit, while a second-story balcony overlooks the outdoor area, offering views of the forest.

5 out of 5 average rating, 47 reviews

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