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Holiday rentals with a kayak in Columbia County

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Top-rated Accommodation with a Kayak in Columbia County

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Home in Athens

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.

ValueLocationBathroom

4.95 out of 5 average rating, 192 reviews
Superhost
An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.
Holiday home in Athens

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

Outdoor spacesLocationCheckout

4.86 out of 5 average rating, 128 reviews
Top Guest favourite
Aerial view captures a serene lake surrounded by autumn foliage. The vibrant colors of the trees reflect on the calm water, with a small island at the center. Lush greenery contrasts with the warm hues, providing a peaceful natural setting.
Island in Pine Plains

Magical Private Island Retreat in Pine Plains

Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

Outdoor spacesValueView

4.97 out of 5 average rating, 110 reviews
Top Guest favourite
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

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

LocationOutdoor spacesGetting around

4.95 out of 5 average rating, 256 reviews
Top Guest favourite
A two-story historic home is showcased with blue siding and white trim. The front porch features a railing and is lined with flower beds. Windows are adorned with dark frames, and an air conditioning unit is visible. A driveway leads to a parked vehicle on the side.
Home in Athens

Renovated historic home, walk to Hudson River!

Escape from the city and enjoy slowing down in upstate New York in this bright and spacious historic home! Just a short walk to the historic Town of Athens and the Hudson River where you can sit by the water, enjoy a picnic, or kayak/canoe. This home is made for cozy unwinding and is stocked with everything you need to cook a wonderful meal (cast irons, French cookware, baking supplies, spices and oils). 1 king bed with view of the river, 1 queen bed + a full air mattress available.

LocationValueView

4.94 out of 5 average rating, 128 reviews
Guest favourite
Home in Craryville

Copake Lake Artist Cottage with Dock and Kayaks

Renovated cottage just 500 ft from Copake Lake. This 2 BR 1 bath house is also close to hiking trails, waterfalls, apple picking, & a winery, and in winter, there’s skiing at Catamount (it’s just six miles away!) and a distillery nearby. A house for all seasons! Please note the cottage is 5 houses back and across a quiet road from the lake, and the dock is in the lake from the beginning of May to the end of September. But there is plenty to do up here during the rest of the year!

Outdoor spacesLocationLaundry

4.85 out of 5 average rating, 171 reviews
Guest favourite
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

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

2 hours from NYC+ Boston. 20 minutes to Great Barrington + Hudson, NY. Explore the Hudson Valley + nearby Berkshires (Tanglewood)or enjoy the many pleasures of beautiful Copake Lake + the Berkshire foothills. 8.5 mile to Catamount Ski/Snowbard, 20 miles to Ski Butternut. Bash Bish Falls, Taconic State Park, Tanglewood, Harlem Valley Rail Trail, nearby golf course. Explore quiet country roads, charming nearby towns including Hudson, Chatham, Millerton + Great Barrington, MA.

LocationValueTV

4.82 out of 5 average rating, 136 reviews
Guest favourite
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

Hudson area waterfront-fish, kayak, farm visits!

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!

ValueOutdoor spacesComfort

4.84 out of 5 average rating, 155 reviews
Top Guest favourite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

This newly updated Berkshire lake house with private in-ground pool, is the perfect place for a year-round vacation. Nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. 5 light-filled bedrooms can accommodate a family retreat or 3 families. Enjoy the pool table, chefs kitchen, two living room areas, and wood burning fireplace inside and fire pit outside. All bedrooms and common areas have air conditioning.

LocationOutdoor spacesAmenities

4.99 out of 5 average rating, 101 reviews
Top Guest favourite
Home in Athens

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

LocationOutdoor spacesAccuracy

4.96 out of 5 average rating, 112 reviews
Top Guest favourite
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

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

Outdoor spacesValueGetting around

4.97 out of 5 average rating, 145 reviews
Guest favourite
The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.
Cabin in Athens

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!

ValueLocationBarbecue

4.95 out of 5 average rating, 137 reviews

Popular amenities for Columbia County kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Top Guest favourite
A serene lake is surrounded by lush green hills, reflecting the clear blue sky. The water is calm, with a small rowboat visible in the distance, adding to the tranquil outdoor setting.
Home in Town of Ancram

Friends/Family & A Dog~What Else Could Be Better?

LocationOutdoor spacesCheck-in

4.99 out of 5 average rating, 196 reviews
Top Guest favourite
Home in Athens

All Season Vacation Lakehouse in the Hudson Valley

Outdoor spacesLocationHospitality

4.92 out of 5 average rating, 107 reviews
Guest favourite
A serene lakeside view is captured at sunset, with vibrant pink and purple hues reflecting over the calm water. Silhouetted trees frame the scene, and distant hills provide a tranquil backdrop to the picturesque landscape.
Home in Pine Plains

Twin Island Lake House • Hot Tub

Outdoor spacesLocationAmenities

4.97 out of 5 average rating, 141 reviews
Guest favourite
A rustic boathouse is positioned by a tranquil pond, surrounded by lush greenery and trees. The water reflects the blue sky and fluffy white clouds, creating a serene natural scene. A wooden deck extends towards the water, offering a spot to relax by the edge.
Home in Copake

Unique 30 Acre Waterfront Retreat

Outdoor spacesLocationCondition

4.95 out of 5 average rating, 20 reviews
Guest favourite
A serene view of a tranquil lake reflects the blue sky and surrounding greenery. The outdoor area includes a wooden deck with seating, a grassy lawn, and boats awaiting exploration. Sunlight glints on the water's surface, enhancing the peaceful atmosphere.
Home in Copake

Lakefront Home • Kayaks • Firepit • Near Skiing

Outdoor spacesLocationCheck-in

4.88 out of 5 average rating, 32 reviews
Top Guest favourite
Home in Salisbury

Greystone at Twin Lakes

Outdoor spacesLocationSkiing

4.97 out of 5 average rating, 72 reviews
Top Guest favourite
A view from the cottage steps overlooks a tranquil lake surrounded by lush greenery and trees. Flower pots and garden arrangements add color along the pathway leading toward the water, creating a peaceful outdoor space for relaxation.
Home in Niverville

Cozy Lakeside Retreat

Outdoor spacesLocationKitchen

4.93 out of 5 average rating, 30 reviews
Guest favourite
Home in Copake

Lakefront Retreat w/ Private Dock & Gazebo

Outdoor spacesPetsHospitality

5.0 out of 5 average rating, 5 reviews

Cottages with a kayak

Guest favourite
Cottage in Egremont

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

Outdoor spacesValueComfort

4.98 out of 5 average rating, 55 reviews
Guest favourite
A well-maintained outdoor space features a circular stone fire pit surrounded by multiple Adirondack chairs. Tall trees provide shade, and a nearby cabin is visible alongside a spacious house. Clear blue skies create a bright and inviting atmosphere.
Cottage in Craryville

Fun Getaway Lakehouse in the Hudson Valley

LocationOutdoor spacesCheckout

4.91 out of 5 average rating, 54 reviews
Top Guest favourite
A wooden deck overlooks a serene lake at sunset, with the golden sun reflecting on the water. Comfortable outdoor seating and a large umbrella provide shade, while a glass of wine is held in the foreground, emphasizing a peaceful atmosphere.
Cottage in Niverville

Huge Lakefront, Cozy Private Cottage in Upstate NY

LocationOutdoor spacesHiking

4.98 out of 5 average rating, 51 reviews
Guest favourite
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

Lake Front Cottage with Sun Soaked Terraces

ValueOutdoor spacesQuiet

4.88 out of 5 average rating, 50 reviews
Guest favourite
Cottage in Craryville

Lakeview Cottage w/ Kayaks, Deck, & Lake Access

LocationOutdoor spacesBeach

4.91 out of 5 average rating, 23 reviews
Superhost
The bright and airy kitchen and dining area features high ceilings and modern fixtures. A wooden table with stylish chairs sits at the center, flanked by a sleek kitchen with stainless steel appliances. Natural light flows in through windows, enhancing the clean and open space.
Cottage in Copake

Lakefront Retreat on Robinson Pond

LocationOutdoor spacesLayout

4.84 out of 5 average rating, 64 reviews
Guest favourite
A serene view of a spring-fed lake is framed by trees, with gentle ripples reflecting the blue sky and clouds. Lush greenery surrounds the water's edge, contributing to a tranquil natural setting. The scene highlights the peacefulness of the 26 acres of private land.
Cottage in Valatie

Hudson Lake Resort: MV Buren Cottage III

ValueLocationShared spaces

4.91 out of 5 average rating, 76 reviews
Guest favourite
Cottage in Copake

Modern Mid-Century House -Hike, Kayak, Lake Access

LocationOutdoor spacesBeach

4.92 out of 5 average rating, 131 reviews

Cabin rentals with a kayak

Top Guest favourite
Cabin in Red Hook

Luxury Scandi Lakeside Cabin with Woodfired Sauna

Outdoor spacesLocationSleep quality

5.0 out of 5 average rating, 17 reviews
Top Guest favourite
The cabin features a charming exterior with a blue-gray wooden facade and a bright red door. Large windows provide natural light to the space. Two red Adirondack chairs are positioned on the stone patio, inviting guests to relax in the natural surroundings.
Cabin in Climax

Catskills Cabin on 100 Wooded Acres, Private Lake

LocationOutdoor spacesPets

4.95 out of 5 average rating, 88 reviews
Guest favourite
Cabin in Pine Plains

Robin's Nest: Cozy Lakeside Cottage in Pine Plains

LocationOutdoor spacesLong stay

5.0 out of 5 average rating, 5 reviews
Guest favourite
Cabin in Ghent

Country Retreat

ValueLocationKitchen

5.0 out of 5 average rating, 50 reviews
Guest favourite
Cabin in Athens

Peaceful Lakefront Cabin w/Dock and Kayaks

Outdoor spacesLocationBeach

5.0 out of 5 average rating, 5 reviews
Guest favourite
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 Town of Hillsdale

Cozy Yellow Cabin on Copake Lake

Outdoor spacesLocationTV

4.89 out of 5 average rating, 19 reviews
Cabin in Austerlitz

The Cosmo Cottage

LocationOutdoor spacesIndoor spaces

4.6 out of 5 average rating, 5 reviews
Cabin in Athens

Drift House: Lakefront, Dock, Fire Pit & Views

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