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

4.97 out of 5 average rating, 101 reviews

The living room features exposed wooden beams and warm hardwood flooring. A spacious seating area is centered on a large area rug, surrounded by colorful floor rugs. Framed artwork adorns the walls, while natural light filters in through window treatments.

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 :)

4.94 out of 5 average rating, 346 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

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.

A two-story historic home is showcased with blue siding and white trim. The front porch features a railing and is lined with flower beds. Windows are adorned with dark frames, and an air conditioning unit is visible. A driveway leads to a parked vehicle on the side.

4.94 out of 5 average rating, 105 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.

Superhost

The spacious living area features warm wooden flooring and exposed brick walls. A gas fireplace is positioned centrally, surrounded by comfortable seating. Dining furniture is visible nearby, along with a staircase leading to upper levels, illuminated by natural light from multiple windows.

Apartment in Hudson

4.9 out of 5 average rating, 319 reviews

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.

4.94 out of 5 average rating, 139 reviews

A seating area is positioned near the water's edge, featuring four blue Adirondack chairs and a reclining chair on a gravel surface. In the background, a white lighthouse stands, overlooking the calm river and lush green trees lining the shore.

Loft in Athens

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.

A lakeside deck features two red Adirondack chairs and a small side table, providing a perfect spot for relaxation. The serene waters reflect the greenery of trees and distant homes, while a nearby dock accommodates several boats. Clear skies enhance the tranquil atmosphere.

4.91 out of 5 average rating, 22 reviews

Cozy Lakefront Home in Athens

Relax in a cozy and comfortable lakefront house in nature, gazing at the lake with a cup of coffee and feel like you’re at home. Watch the fall foliage with your loved ones and enjoy the community pool in the summer, sun tan and swim at the convenient lake beach or from our private dock. All on Lisa Lane! This 3 bedroom, 2 bath will make you feel like you’re not at an Airbnb, but relaxing at home. Swim, fish, tennis, golf, ski and snowboarding! And only minutes from the chic town of Hudson!

The lakefront house is illuminated at night, showcasing a welcoming glow from the large windows. String lights create a festive atmosphere on the wraparound deck, complemented by Adirondack chairs and a fire pit area, surrounded by lush greenery.

4.93 out of 5 average rating, 27 reviews

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.

A spacious deck features sleek, dark chairs lined up for relaxation, with a table set conveniently for outdoor dining. The surrounding trees provide a natural backdrop, while expansive windows on the house offer views of the lakeside scenery.

4.91 out of 5 average rating, 33 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.

4.98 out of 5 average rating, 154 reviews

A scenic view is captured from a deck, showcasing a calm pond reflecting vibrant autumn foliage. A rustic vase of flowers is placed on a railing, while the sky displays a gradient of soft pinks and purples as the sun sets behind the hills.

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.

4.89 out of 5 average rating, 115 reviews

A spacious lakefront home is nestled among tall trees, with a sloping green lawn leading to the deck. The house features a distinctive A-frame design with large windows, allowing natural light to fill the interior. Shadows from the surrounding trees enhance the serene outdoor setting.

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, 124 reviews

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

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.