Family-friendly holiday rentals in Sleepy Hollow Lake, Greene County, New York

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Top-rated family-friendly rentals in Sleepy Hollow Lake, Greene County, New York

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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
4.88 out of 5 average rating, 113 reviews

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

Top guest favourite
A pass-through window features a wooden countertop, displaying decorative items and a candle. A vibrant blue refrigerator and various kitchen appliances are visible in the background. The space is brightened by natural light, creating a cheerful ambiance.
Cottage in Catskill
4.96 out of 5 average rating, 306 reviews

1930's Cottage charm cozy air cond. near hiking

1 bedroom 1930's guest cottage with a living room. Near many hiking trails. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.

Superhost
The interior of a rustic cabin features timbered walls and ceilings, with large glass windows offering views of the surrounding foliage. A wood-burning stove is positioned on a stone base, while a white door leads outside. Shelves hold a selection of books.
Tiny home in Palenville
4.87 out of 5 average rating, 175 reviews

Unique Tiny House Glamping in the Catskills

Looking for the perfectly romantic glamping getaway? This stunning handcrafted hut was designed by my Buddhist mother for a meditation retreat, and to commune with nature. With unique timbered walls and ceilings, a wood-burning stove (the only heat source), rustic stone detailing on the walls and large glass windows, you'll feel like you're living in the woods, but with the comfort of the indoors. Please note that this is an off-grid camping cabin without water, but there is electricity.

Guest favourite
An aerial view captures the serene landscape surrounding the red barn, nestled among lush green fields. Pastures and trees create a tranquil setting, with distant farmland visible in the background, providing a sense of seclusion in the countryside.
Farm stay in Kinderhook
4.87 out of 5 average rating, 247 reviews

Barn House: isolated sheep farm Hudson area

April lambing, October leaf peeping, summer swimming, winter by the stove: A century-old brick barn, eclectic style, much art, 10 miles from Hudson, near Kinderhook, secluded, unique residence. Gardens, sheep, and ponies are set off a country road, with a converted jungle shower, loft, and woodstove. Waterfall swimming area nearby. Empire bike path, e-bikes by request. Hudson Valley. The farm shares space with nature as it is - country life. Pony rides for children by prior arrangement.

Guest favourite
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, 121 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.

Top guest favourite
A friendly horse leans through an open window, with soft curtains framing its gentle face. The horse's striking black and white markings are visible, while light filters softly into the room, highlighting the welcoming ambiance.
Flat in Coxsackie
4.97 out of 5 average rating, 170 reviews

Susie's Climax Creations

Susie's Climax Creations Farm is where you can experience a stay on a farm. The charming farm house is roughly 200 years old, located 2.5 hours from NYC, 25 minutes from the Hudson train station. If you want to stay somewhere safe from Covid-19 exposure this is the place! Susie's Climax Creations is on a quiet dead end street. The apartment has a private entrance and completely self contained. If you would like to see more of the farm animals check out my site located at Kliese140.

Top guest favourite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Flat in Coxsackie
4.99 out of 5 average rating, 139 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Guest favourite
A yellow sign is displayed among green foliage, featuring a goat and two ducks illustrated on it. The bold text indicates 'SLOW FREE RANGE DUCKS & GOATS at PLAY,' emphasizing the friendly atmosphere surrounding the property.
Farm stay in Ancram
4.96 out of 5 average rating, 362 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

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
4.95 out of 5 average rating, 114 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!

Superhost
The tiny house is surrounded by a snow-covered landscape, showcasing large windows that allow warm light to emanate from within. The wooden structure features a combination of solid walls and expansive glass sections, creating a cozy atmosphere amid the winter scenery.
Tiny home in Catskill
4.86 out of 5 average rating, 179 reviews

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

A really really tiny house ,( smaller than most tiny houses) with a dome patio for viewing the sky. Two hours from NYC, close to skiing (hunter mountain/ Windham, Kaaterskill falls, Woodstock, Hudson, Saugerties. We have - Heat/AC, Queen bed, Hot shower, Flushing Toilet, Kitchenette, Fridge, Towels, linens etc. *Hudson Getaways is a small woman owned business. We offer discounts to our social media followers and to returning guests .

Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.98 out of 5 average rating, 116 reviews

Contemporary Cabin in Catskill Mountains

Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. Ready to escape the ordinary? Book your stay today.

Guest favourite
A well-lit studio space features a spacious bed dressed in white linens with decorative pillows. Light wooden cabinets and a dining table with four chairs are visible in the background, complemented by a full kitchen equipped with essential appliances.
Guest suite in Hudson
4.94 out of 5 average rating, 206 reviews

Harmony Valley Home, bright & inviting studio

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries & breweries Museums & art Hiking trails Empire State Rail Trail Conservation Areas Shopping

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