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

Lakefront | Hot Tub | Game Room | Movie Theater

🌲 Wanderwood Lakehouse | Sleeps 10 | Hot Tub • Theater • Game Room • Dock 🌊 Reset & 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.

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

Lakefront Luxury: Private Hudson Valley House

Escape to The Billingswood, a stunning retreat on the shores of Sleepy Hollow Lake in Athens, NY! This 3BR, 3BA home offers 150+ feet of private lakefront, a sunroom, a game room, and multiple decks—including an overwater deck for breathtaking views. Relax in the cozy living spaces, enjoy alfresco dining with the outdoor grill, and take advantage of community pools, tennis, golf courses and more. With space for up to 8 guests, this getaway blends comfort, recreation, and serene lakefront living.

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.

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!

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.

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.

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.

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.