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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Guest favorite

Apartment in Athens

4.93 out of 5 average rating, 215 reviews

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.

Top guest favorite

Home in Athens

4.97 out of 5 average rating, 35 reviews

Private Lake House Surrounded by Nature

See the stunning sunset from the deck at our log cabin style lake house. Enjoy gorgeous lake views from the open living space flooded with natural light. Take a kayak out from the private dock & enjoy a peaceful evening around the fire pit. Relax as you'll be surrounded by nature! Inside find: fireplace, workspace, rec room, laundry, games, baby equip. Take advantage of all the community has to offer: pools, beach, tennis, pickleball & b ball courts & more! Situated close to NYC, Hunter & Windam

Guest favorite

Home in Athens

4.93 out of 5 average rating, 123 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

A historic two-story stone building is complemented by a smaller adjoining structure. Lush green lawns surround the buildings, and trees provide shade. The background showcases the Hudson River, reflecting a soft evening light with the moon rising above. Outdoor seating areas are visible along the shore.

Loft in Athens

4.93 out of 5 average rating, 135 reviews

1860 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.

Guest favorite

A fire pit surrounded by sparkling glass stones illuminates the space with a warm glow. Above the pit hangs a wooden sign featuring the name "Wanderwood Lakehouse," creating a welcoming focal point for evening gatherings.

Home in Athens

4.96 out of 5 average rating, 45 reviews

Lux Lakefront | Dock | Game Room | Movie Theater

🌲 Wanderwood Lakehouse | Sleeps 10 | Theater • Game Room • Dock 🌊 Reset and relax at this serene lakefront retreat where nature meets adventure and comfort meets luxury - welcome to the Wanderwood Lakehouse at Sleepy Hollow Lake. Nestled on 80 ft of private shoreline, the 3-bed, 2.5-bath oasis sleeps 10 & offers unforgettable views, surrounded by whispering trees & tranquil water in the charming river town of Athens - Catskills region of the Hudson Valley - 20 minutes to Hudson, NY.

Guest favorite

Home in Athens

4.96 out of 5 average rating, 25 reviews

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.

Top guest favorite

A vibrant red house is nestled amidst lush greenery, overlooking a serene pond. Colorful wildflowers frame the foreground, while gentle slopes lead to a backdrop of trees. The clear blue sky enhances the tranquil atmosphere of this picturesque setting.

Place to stay in Leeds

4.98 out of 5 average rating, 146 reviews

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.

Guest favorite

A spacious dining area is illuminated by natural light from large windows. A large wooden table is surrounded by white chairs, complemented by a cozy seating area with a grey armchair. The warm wood ceiling adds a rustic touch, enhancing the open atmosphere.

Chalet in Athens

4.9 out of 5 average rating, 107 reviews

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.

Guest favorite

A compact laundry area is visible within a closed door. A stacked washer and dryer set is positioned neatly, with detergent placed on top. The white appliances are set against a subtle backdrop, maintaining a clean and organized appearance.

Apartment in Hudson

4.97 out of 5 average rating, 302 reviews

Stylish Hudson Getaway

Enjoy our one bedroom home in the heart of beautiful Hudson, New York. Steps away from the best shops and restaurants Warren Street has to offer, our apartment is on a beautiful residential street with historic views. Introduce yourself to our town with the peace of mind that when you return to this Airbnb, you can relish in the delight of organic cotton sheets, lush robes and slippers, an assortment of organic teas and coffee, and some of the best products from our sweet little city.

Top guest favorite

A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.

Apartment in Coxsackie

5 out of 5 average rating, 119 reviews

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.

Guest favorite

A serene view of the lake is framed by branches of a tree, showcasing a soft gradient of colors in the sunset sky. The calm water reflects the hues of pink and purple, while the dock is visible along the water's edge.

Cabin in Athens

4.94 out of 5 average rating, 105 reviews

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!

Guest favorite

Cabin in Saugerties

4.98 out of 5 average rating, 205 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

A stunning modern update to a classic A-frame design. This brand new 1000 square foot home is big enough to accommodate up to four guests with a lofted master king bedroom and queen lower bedroom. The house includes a full kitchen, bathroom, mudroom, office and a wrap around deck to take in the mountain views. Nestled on a sprawling 15 acre lot with private pond and hiking trails. The ultimate getaway for the discerning traveler.