
Vacation rentals in Sleepy Hollow Lake, Greene County, New York
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Top-rated vacation rentals in Sleepy Hollow Lake, Greene County, New York
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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.

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

Modern & Cozy Lake Oasis ~ Hot Tub ~ 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. ✔ Game Room ✔ Private Hot Tub, BBQ, Fire Pit ✔ Lake Access (2 Kayaks, Paddleboard) ✔ High-Speed Wi-Fi ✔ Community Amenities (Seasonal Pools, Sports) Perfect for families and groups looking to relax. Not suitable for parties. Please note: nearby construction on adjacent properties occurs M–F and may be audible in parts of the home.

Winter Escape/Lakeview Hideaway/ExpansiveLakeHouse
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

Tiny Home A-Frame with Hot Tub & Creek
Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Lakeside home with fireplace near skiing
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.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

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.

Cozy Catskill Getaway by Hudson
Tucked away in the Sleepy Hollow Lake community, this charming A-frame is the perfect retreat for those seeking a blend of rustic charm and modern comfort. Just a short walk from the lake, the house offers open concept living space, fully equipped kitchen, 3 bedrooms and 2 1/2 baths. Unwind by the wood burning stove, challenge your friends to a game of pool, or step outside to soak in the private hot tub or to sit by the firepit and roast marshmallows under a canopy of stars.

Riverfront, Fireplace, 20 min to Hudson & Windham
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.

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. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Cozy Lakefront Retreat: Hot Tub & Fireplace
🌲 Hot Tub • Plexiglass Star-Gazing Dome • Theater • Game Room • Kayaks Wanderwood Lakehouse — a serene Catskills vacation rental on 80 ft of private shoreline. This 3-bed, 2.5-bath oasis sleeps 8 with stunning lakefront views, private large dock & easy access to hiking trails, waterfalls, fly fishing & ski resorts. Nestled in Athens, just 20 min to Hudson, NY — perfect for a family vacation, cozy couples getaway, or Upstate NY adventure.
Popular amenities for Sleepy Hollow Lake, Greene County, New York vacation rentals
Other great vacation rentals in Sleepy Hollow Lake, Greene County, New York

Peaceful, Low Toxin Haven

Brand New Lakefront Retreat! Kayaks/Firepit/Games

White Bunny Cottage

Stylish Pet-Friendly Retreat w/ Hot Tub

Modernist Upstate Retreat

Modern farm house 4 beds 3 baths 15 mins to Hudson

Lake house, 700 ft waterfront - from every room

Stylish Home on Union St
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- Family-friendly rentals Sleepy Hollow Lake, Greene County, New York
- Rentals with outdoor seating Sleepy Hollow Lake, Greene County, New York
- Rentals with a washer and dryer Sleepy Hollow Lake, Greene County, New York
- Rentals with lake access Sleepy Hollow Lake, Greene County, New York
- Rentals with a fireplace Sleepy Hollow Lake, Greene County, New York
- Rentals with a fire pit Sleepy Hollow Lake, Greene County, New York
- Rentals with a patio Sleepy Hollow Lake, Greene County, New York
- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Windham Mountain
- John Boyd Thacher State Park
- Howe Caverns
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Norman Rockwell Museum
- Hunter Mountain Resort
- Taconic State Park
- Plattekill Mountain
- Bousquet Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Mohawk Mountain Ski Area
- Beartown State Forest
- Opus 40
- Albany Center Gallery
- Berkshire Botanical Garden
- Peebles Island State Park




