Vacation rentals in Sleepy Hollow Lake, Greene County, New York

4.96 out of 5 average rating, 103 reviews

Cottage in Catskill

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 :)

4.93 out of 5 average rating, 217 reviews

Apartment in Athens

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.

4.96 out of 5 average rating, 55 reviews

Catskills Lake Retreat-Hot Tub, Dome, Fall Foliage

🌲 Upstate NY Lakehouse • Hot Tub • Dome • Theater • Game Room • Kayaks Reset & relax at Wanderwood Lakehouse — a serene Catskills vacation rental on 80 ft of private shoreline. This 3-bed, 2.5-bath oasis sleeps 10 with stunning lakefront views, vibrant Catskills fall foliage & easy access to hiking trails, waterfalls, kayaking, fly fishing & ski resorts. Nestled in Athens, Hudson Valley, just 20 min to Hudson, NY — perfect for a family vacation, cozy couples getaway, or Upstate NY adventure.

4.98 out of 5 average rating, 42 reviews

Expansive Lake House/Private Dock/Stunning Views

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

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.

4.94 out of 5 average rating, 145 reviews

Loft in Athens

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.

Superhost

4.86 out of 5 average rating, 37 reviews

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.

4.98 out of 5 average rating, 163 reviews

Place to stay in Leeds

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.

4.88 out of 5 average rating, 119 reviews

Chalet in Athens

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.

5 out of 5 average rating, 128 reviews

Apartment in Coxsackie

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.

4.99 out of 5 average rating, 462 reviews

Bungalow in Cairo

Riverfront, Fireplace & Fire Pit -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.