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 · Location · Outdoor spaces

Catskills Lakehouse-Fall Foliage -Cozy Fireplace

As the year turns, our Lakehouse offers a new experience each season. In fall & winter, watch fiery foliage or snowfall from the deck, cozy up by the fireplace, & unwind in the jacuzzi after days of apple‑picking or skiing. In spring and summer, the lake becomes your playground—launch kayaks & paddleboards from the private dock, dine al fresco on the deck with a gas grill, & enjoy the community pool & beach. The home adapts to every mood, ensuring unforgettable memories no matter when you visit.

Family · Location · Hospitality

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 · Location · Layout

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.

Location · Family · Walkability

The Happy Place

Escape with the whole family to our beautiful lakefront house. Our home is located on beautiful Sleepy Hollow Lake nestled amid the glorious natural countryside of the Hudson Valley and Catskill Mountains. This is your cozy getaway. Enjoy water activities during the day, then relax under the stars by our toasty fire pit or a dip in the hot tub. We're a short distance from some of the trendiest upstate restaurants, bars and shops and have one of the most picturesque views of the lake.

Location · Family · Accuracy

Lakeside home kayaking, and close to Hudson

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.

Family · Location · Access

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.

Location · Value · Accuracy

Athens Cottage

Welcome to your perfect Hudson Valley escape. This cozy two-bedroom cottage is nestled in the charming riverside village of Athens, NY, offering small-town charm, scenic beauty, and a relaxing home base for your stay. Inside, you’ll find a thoughtfully furnished space filled with natural light, comfortable bedrooms, and all the essentials for a stress-free getaway. Whether you’re sipping coffee in the morning or unwinding after a day of exploring, the cottage feels warm and inviting.

Family · Location · Condition

Casa del Lago · Private Lake, pools, tennis court

Peaceful Family Retreat | Lake/ beach /Pools • Ski • Hike Unplug and recharge 2 hrs from NYC—where nature, comfort, and adventure meet. Near Hudson and the Catskills, this serene home offers year-round fun: pools, beach (10-min walk), tennis, pickleball, basketball, driving range, and playgrounds. Enjoy nearby hiking, dining, wineries, and breweries. Celebrate fall with apple picking, pumpkin patches, sunflower fields, and festivals. Ski Hunter and Windham are just 30 mins away.

Family · Value · Walkability

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!

Family · Value · Comfort

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!

Value · Family · Skiing

Larkspire | Sleepy Hollow Lake | Beach & Firepit

Larkspire by the Lake is your escape from the city — a fully renovated 3-bedroom home sitting inside Sleepy Hollow Lake, a private gated community in the Catskills. Walk to a private beach, lake, and pool. Come back to a firepit, a warm deck, and a house that actually feels like home. This is the kind of place where the first morning coffee on the deck makes you forget you were ever stressed. Two hours from NYC, a world away.

Family · Location · Hospitality