Holiday houses in Sleepy Hollow Lake, Greene County, New York

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.

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.

Warren St. Ensuites - Pets allowed

Just 2 doors west of the coveted 4 star Maker Hotel, this is 1 of the most desired locations in Hudson. Featuring 4 gas fireplaces, original flooring, exposed brick walls, 3 bedrooms of which 2 ensuites include king & pull out love-seat, & whirlpool. Third large bedroom contains queen bed. A perfect couples getaway. "Comfortable, tasteful, private and right in the heart of Hudson". The Living Room, ensuites, library & dining area have ceiling fans - that keep you cool with/without a/c.

Lakeside home with Private dock and more !

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.

The Ice House on Mill Pond

Escape to this picturesque setting nestled along the Catskill Creek, with private deck and awe-inspiring views of the pond, cliffs and rapids. Whether seeking a serene romantic getaway or a chance to recharge, this unique spot provides a harmonious blend of comfort and nature. Immerse in the soothing flow of nature and indulge in some of the best offerings in the Hudson Valley. Inside, the house is clean and cozy, providing the ideal haven to unwind and reconnect with your surroundings.

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.

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.

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View

Welcome to my spacious and entertaining lakefront getaway nestled on the shores of the picturesque Sleepy Hollow Lake! Grab the kayak and explore the lake or lounge the day away in the hot tub. ✔ Game Room ✔ Private Hot Tub, BBQ, Fire Pit ✔ Lake Access (2 Kayaks, Paddleboard) ✔ High-Speed Wi-Fi ✔ Community Amenities (Seasonal Pools, Sports) Please note: nearby construction on adjacent properties occurs M–F and may be audible in parts of the home.