Family-friendly vacation 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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Guest favorite

The living room features exposed wooden beams and warm hardwood flooring. A spacious seating area is centered on a large area rug, surrounded by colorful floor rugs. Framed artwork adorns the walls, while natural light filters in through window treatments.

Cottage in Catskill

4.97 out of 5 average rating, 102 reviews

Cozy Catskill Cottage

Kick back and relax in this serene and stylish mid-century cottage. Perched atop a knoll and shaded by a giant oak, the enchanting property hosts a juniper grove, apple trees, wildflowers, wild raspberries and blackberries. The backyard oasis consists of a gravel picnic area, patio, firepit flanked by Adirondack chairs and ample grassland for yard games. Have your morning coffee on the front porch rocking chairs and take in the surroundings. This is a quiet place to relax, no parties please :)

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.

Home in Athens

4.95 out of 5 average rating, 152 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.

Guest favorite

A spacious bedroom features floral wallpaper with green and pink patterns. A wooden bed is draped with a red patterned coverlet and accented by a decorative pillow. Two windows allow for natural light, and a bedside table with a lamp complements a nearby chair.

Apartment in Athens

4.93 out of 5 average rating, 217 reviews

1 bdrm apt in Athens on the Hudson

Come enjoy village life right in the middle of this friendly and vibrant, yet quiet community in your own charmingly appointed 3 room apartment. Explore the Great Northern Catskills with its boating and paddling opportunities, antiquing, local history, art and music. The Thomas Cole House is minutes away in Catskill. Olana is right across the Rip Van Winkle Bridge. If sculpture is your passion, Opus 40 in Saugerties is not to be missed. Winerys abound and be sure not to miss Athens own brewery.

Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 352 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Top guest favorite

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

4.94 out of 5 average rating, 106 reviews

Renovated historic home, walk to Hudson River!

Escape from NYC and enjoy a slower pace in this bright and spacious historic home, just a short walk to the Hudson River where you can sit by the water, enjoy a picnic, or kayak. This home is made for entertaining and is stocked with everything you need to cook a wonderful meal (cast irons, French cookware, baking supplies, spices and oils). There is a little view of the river from the backyard where you can also build a fire. 1 queen bed, 1 full bed and one full air mattress also available.

Guest favorite

A seating area is positioned near the water's edge, featuring four blue Adirondack chairs and a reclining chair on a gravel surface. In the background, a white lighthouse stands, overlooking the calm river and lush green trees lining the shore.

Loft in Athens

4.94 out of 5 average rating, 143 reviews

1860's Carriage House Loft on Hudson River

Carriage house apartment on grounds of historic 1600's Dutch bouwerij (farm), yet with all of the modern amenities. Our Hudson river side apartment features original exposed beams, wood floors, tasteful decor, and a complete country kitchen. On-Hudson river edge setting with beach access allows watching eagles & herons, or kayaking. Walk-in to marshland wildlife refuge. 19th century lighthouse on property. Leaf peeping or apple picking during the fall. Hunter and Windham ski areas nearby.

Guest favorite

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, 117 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.

Guest favorite

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.

Apartment in Coxsackie

4.97 out of 5 average rating, 159 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 favorite

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.

Apartment in Coxsackie

5 out of 5 average rating, 126 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.

Top guest favorite

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

4.97 out of 5 average rating, 349 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 favorite

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

4.94 out of 5 average rating, 108 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!

Top guest favorite

A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.

Cabin in Saugerties

4.98 out of 5 average rating, 220 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Sleek 2‑BR A‑frame pairs timeless design with modern luxury in a secluded Catskills setting. Soak in the cedar barrel sauna after a day on the trails, then watch sunsets from the wrap‑around deck framing mountain views. Lofty king suite, cozy queen room, chef’s kitchen, bathtub, mudroom entrance, and office nook for remote work. Propane webber grill, smokeless fire pit, fast Wi‑Fi, and smart‑lock entry—your elevated escape awaits!