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

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Top-rated holiday rentals in Sleepy Hollow Lake, Greene County, New York

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Superhost

An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.

Holiday home in Athens

4.86 out of 5 average rating, 127 reviews

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

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Top guest favourite

Home in Athens

4.98 out of 5 average rating, 66 reviews

Catskills Lakehouse-Fall Foliage -Cozy Fireplace

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.

LocationFamilyNearby

Guest favourite

A two-story lake house is presented under a clear blue sky, featuring a brown wooden exterior and a spacious front yard. The driveway leads to a two-car garage, with double garage doors that add to the home's charm. Surrounding greenery enhances the peaceful setting.

Home in Athens

4.84 out of 5 average rating, 32 reviews

Mountain-view Escape

Forget your worries in this spacious and serene lake house. 4 BR , 2.5 B (a master bedroom with full bath en-suite) can fit up to 10 guests. 30 minutes away from Windham and Hunter mountain ski. 40 min away from Kaaterskill Falls. Minutes away from Sleepy Hollow Lake with beach access, tennis, basketball, volleyball courts + 2 pools (seasonally) Enjoy a cup of coffee or tea on our screened in porch or by the fire out back. Boasting two spacious living rooms for tv watching, game play and fun!

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Guest favourite

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, 164 reviews

1860's Hudson River Carriage House Loft

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.

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Top guest favourite

Home in Athens

4.92 out of 5 average rating, 107 reviews

All Season Vacation Lakehouse in the Hudson Valley

Enjoy the perfect all-season getaway at our beautiful lake house in New York's Hudson Valley. From this central location, you can explore the towns of Athens, Hudson, Catskill, and Coxsackie. Visit antique shops, explore outdoor trails, and try local cuisine. In summer, the personal dock allows for kayaking on the lake. Easy beach access, parking, and a beautiful pool await. In winter, cozy up next to the fireplace and firepit. Enjoy nearby skiing at Hunter, Catamount, and Belleayre.

LocationFamilyOutdoor spaces

Superhost

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.

Home in Athens

4.95 out of 5 average rating, 41 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.

LocationFamilyTV

Top guest favourite

A cozy A-frame retreat is set against a clear blue sky, featuring a spacious deck that extends from the home. Large windows are positioned on the upper levels, allowing ample natural light to fill the interior. Lush greenery surrounds the property, enhancing its serene appeal.

Home in Athens

4.97 out of 5 average rating, 29 reviews

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.

FamilyValueAccuracy

Top guest favourite

A spacious game room features dual large screens for entertainment, along with a sleek shuffleboard table and a pool table. A modern kitchenette is positioned in the corner, and warm wood flooring enhances the inviting atmosphere.

Home in Athens

4.98 out of 5 average rating, 93 reviews

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!

LocationFamilyCleanliness

Top guest favourite

Home in Athens

4.96 out of 5 average rating, 112 reviews

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

LocationFamilyLayout

Guest favourite

The kitchen features green cabinetry with a white countertop. Shelves above hold various jars and glasses. A window allows natural light to brighten the space, with a view of nature visible outside. Additional storage includes a fridge and a stainless steel trash bin.

Cabin in Athens

4.96 out of 5 average rating, 135 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!

ValueFamilyAccuracy

Top guest favourite

Home in Athens

5.0 out of 5 average rating, 13 reviews

Larkspire | Sleepy Hollow Lake | Beach & Firepit

Larkspire by the Lake is your escape from the city — a fully renovated 3-bedroom home sitting inside Sleepy Hollow Lake, a private gated community in the Catskills. Walk to a private beach, lake, and pool. Come back to a firepit, a warm deck, and a house that actually feels like home. This is the kind of place where the first morning coffee on the deck makes you forget you were ever stressed. Two hours from NYC, a world away.

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Superhost

Home in Hudson

4.92 out of 5 average rating, 147 reviews

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

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