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

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

Family · Kitchen · Access

1860's Hudson River Carriage House Loft

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.

Family · Kitchen · View

All Season Vacation Lakehouse in the Hudson Valley

Enjoy the perfect all-season getaway at our beautiful lake house in New York's Hudson Valley. From this central location, you can explore the towns of Athens, Hudson, Catskill, and Coxsackie. Visit antique shops, explore outdoor trails, and try local cuisine. In summer, the personal dock allows for kayaking on the lake. Easy beach access, parking, and a beautiful pool await. In winter, cozy up next to the fireplace and firepit. Enjoy nearby skiing at Hunter, Catamount, and Belleayre.

Kitchen · Indoor spaces · Laundry

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.

Indoor spaces · Kitchen · Long stay

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.

Indoor spaces · Family · Accuracy

Hudson River Sunset Getaway

With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Kitchen · Family · Comfort

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.

Kitchen · Family · Walkability

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!

Family · Indoor spaces · Amenities

The Catskill Equestrian Cabin

Decompress in this beautiful, calm, serene new cabin build nestled in the mountains on a peaceful, private five acre lot, bordering an equestrian center. Walk less than two minutes to see the horses during your stay. The cabin is less than 15 minutes to Windham mountain for winter skiing and under 20 minutes to the popular town of Catskill. This cabin has all the amenities you need for a wonderful stay. We hope to host you soon!

Family · Kitchen · Sleep quality

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

Family · Kitchen · Condition

Hudson Valley Lake · Hot Tub · Dock · Games · View

Welcome to my lakefront getaway nestled on the shores of picturesque Sleepy Hollow Lake! Grab the kayak and explore the lake or lounge the day away in the hot tub. ✔ Private Hot Tub, BBQ, Fire Pit ✔ Lake Access (Dock, 2 Kayaks, Paddleboard) ✔ Pool Table ✔ High-Speed Wi-Fi ✔ Community Amenities (Seasonal Pools, Sports) Perfect for families and groups looking to relax. Not suitable for parties.

Family · Kitchen · View

Susie's Climax Creations

Susie's Climax Creations Farm is where you can safely experience a stay on a farm where everyone is welcome! The charming farm house is roughly 200 years old, located 2.5 hours from NYC, 25 minutes from the Hudson train station. Susie's Climax Creations is on a quiet dead end street. The apartment has a private entrance and completely self contained.

Family · Indoor spaces · Access