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

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

Lakefront Luxe Retreat | Beach, Pools, Pickleball

The Billingswood sits on 150+ feet of private Sleepy Hollow Lake shoreline. Start slow in the sunroom, then chase sunset on the overwater deck with wide-open views. Inside: open living + stocked kitchen, game room (foosball + hoops), luxe linens, and 3 full baths. Outside: covered patio, balcony, grill, and an electric firepit. Resort-style community amenities include 2 pools, sand beach, marina, kayak launches, fishing, 5 pickleball courts, tennis, dog park + dog beach, sports complex, golf dri

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.

Lakefront hot tub, dock + kayaks near Hudson

Boutique Catskills Lakefront Rental with Hot Tub, Private Dock & Theater | 20 Min to Hudson, NY Looking for a boutique Catskills lake house with a hot tub near Hudson, NY? Wanderwood Lakehouse is a 3 bedroom, 2.5 bath lakefront rental in Athens, NY that sleeps 8, set on 80 feet of private shoreline. This is where boutique design meets lakefront serenity. Family ready. Dog friendly. Warmly hosted. Also check out the sister property, the Wanderwood Cottage: airbnb.com/h/wanderwoodcottage

Welcome to Casa Bartolo, Your Oasis on the Hudson!

It's now Lilac season! Why book a hotel when you can enjoy a charming, private 2-bedroom suite with breathtaking views of the Catskill Mountains, Hudson River, and stunning sunset! This tranquil retreat offers: Private Entrance, Private shared Bathroom, Kitchenette, cedar soaking tub & easy parking. Wake up to the sunrise and enjoy a cup of Nespresso or tea. Whether you want to relax, walk, jog, bike, meditate, smell the lilacs & pick eggs or simply unwind, this is the perfect escape.

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.

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.

Athens Cottage

Welcome to your perfect Hudson Valley escape. This cozy two-bedroom cottage is nestled in the charming riverside village of Athens, NY, offering small-town charm, scenic beauty, and a relaxing home base for your stay. Inside, you’ll find a thoughtfully furnished space filled with natural light, comfortable bedrooms, and all the essentials for a stress-free getaway. Whether you’re sipping coffee in the morning or unwinding after a day of exploring, the cottage feels warm and inviting.

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.

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Nestled beside a charming creek, our newly renovated cabin offers a peaceful escape where nature and comfort come together. Relax with your partner in the hot tub, on the covered deck, unwind in the wood-fired sauna, or sit by the fire in the gazebo. Enjoy the calming sounds of the creek and the outdoor views from every window. Discover nearby trails, quaint towns, lakes and waterfalls. Pet-friendly and ideal for couples looking for a unique getaway any time of year.

Hot Tub with Pond-front Firepit and Hiking Upstate

Welcome to your dream getaway . Sleepy Hollow offers a variety of premium amenities, including beach access, multiple swimming pools, tennis courts, basketball courts, ensuring there’s something for everyone to enjoy. Additionally, the charming towns of Hudson and Catskills are just 15 minutes away and is renowned for its vibrant culinary scene, art galleries, and antique shops. Albany, New York’s capital, is a short 30-minute drive from the property.

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.