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

4.93 out of 5 average rating, 214 reviews

Apartment in Athens

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.

4.94 out of 5 average rating, 338 reviews

An open living space features a light-colored sectional sofa arranged around a low wooden coffee table. A sleek dining area with chairs is visible, alongside a well-stocked bookshelf and a grand piano. Natural light illuminates the room, enhancing the modern design elements.

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.

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.

4.93 out of 5 average rating, 135 reviews

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

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.

4.96 out of 5 average rating, 24 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, 143 reviews

A private deck overlooks a calm body of water, framed by lush greenery and rocky cliffs. A green table and two matching chairs are positioned to enjoy the scenic view, inviting relaxation and contemplation in a serene outdoor setting.

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.

A covered porch features a white wicker seating arrangement, including a table and chairs. The view extends beyond the railing to the calm waters of the Hudson River, with greenery visible on the opposite bank. A sense of tranquility is evident in this outdoor space.

4.84 out of 5 average rating, 172 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

4.9 out of 5 average rating, 105 reviews

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, 115 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.

4.99 out of 5 average rating, 438 reviews

Large windows frame a view of vibrant autumn foliage, with shades of green and gold visible in the trees outside. Two stylish chairs are positioned in front of the windows, inviting relaxation while enjoying the scenic landscape.

Bungalow in Cairo

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

4.92 out of 5 average rating, 232 reviews

A bright bathroom features a white clawfoot tub and a shower curtain. Black and white tiled flooring adds visual interest, while a window dressed with a light curtain allows natural light to filter in. Bird motifs adorn the walls, enhancing the space.

Apartment in Catskill

Catskill Village House - Mountain View Studio

Our largest option, the Mountain View Suite incorporates high ceilings, and mountaintop views from a raised dining area to provide a large and light oasis. Located on the second floor, the suite features custom antique accents and original artwork that evoke a sense of adventure. The room includes a large bath with clawfoot tub and shower, kitchenette, and sleeper sofa. Custom queen mattress (featured at the Four Seasons NYC), organic cotton sheets.

4.95 out of 5 average rating, 294 reviews

A charming cabin is set amidst greenery, featuring a wooden deck with a small table and two chairs. The facade is painted in a light color, with large glass doors that open to the outdoors. Two contemporary lights are mounted above the entrance.

Tiny home in Saugerties

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! Ac cools beautifully in summer! The Haven at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

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Popular amenities for Sleepy Hollow Lake, Greene County, New York vacation rentals

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Other great vacation rentals in Sleepy Hollow Lake, Greene County, New York

4.93 out of 5 average rating, 82 reviews

House on Lake, walk to beach and kayak!

LisaRating, 5 stars1 week ago

This Airbnb is everything described plus so much more! My family of 11 (9 adults and two 2 year olds) had plenty of seating, bedrooms, and kitchen plates and cutlery. The bathrooms were extremely spacious. The house was very kid friendly with lots of books and a game room. There was a canoe, plenty of kayaks, life vests and outside seating. We found everything we needed and more! We would definitely visit again.

5 out of 5 average rating, 22 reviews

Modern 4 season lakefront rental

StephanieRating, 5 stars1 month ago

This place was so perfect for our friendship getaway out of the city! We were able to just relax and felt right at home in Antonia’s house. There was something to keep us busy all day from drinking coffee on the dock to grilling on the deck! I’d highly recommend this place!

A modern kitchen complete with dark green cabinetry and a central wooden island with four metal-framed stools. Open shelves display various kitchenware, and natural light illuminates the space through a window above the sink.

5 out of 5 average rating, 31 reviews

Renovated Village Home

ZachRating, 5 stars6 days ago

Barbara’s home was perfect for a weekend getaway with friends. Check-in was easy, the home was beautiful and spotless, and was very comfortable. We enjoyed our stay in Athens, with a breakfast/lunch spot and an evening brewery/pizza spot both only one block away! We would certainly stay here again, and would recommend Barbara’s home to anyone!

A winding wooden staircase leads down towards the water's edge, surrounded by lush greenery and vibrant shrubs. The calm lake is visible at the bottom of the steps, with a boat dock partially seen along the shoreline.

4.95 out of 5 average rating, 22 reviews

Lakefront Cabin at Sleepy Hollow

AnnieRating, 5 stars6 months ago

This was one of the best Airbnb stays we’ve had. The place was wonderful and we had a beautiful time in the location. We hope to stay there again in the future.

4.98 out of 5 average rating, 41 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

IzabelaRating, 5 stars5 days ago

My husband and I were blown away by the beauty and thought that was put into this private destination. The moment you step on property, the freshness of the air and sounds of the creek are immediately calming. Diana was incredibly nice and very communicative before and during the entire stay. Activities: The sauna, creek, hot tub, pizza oven, grill, fire place/pits, hammocks- the amenities are amazing and unlike any other Airbnb I have ever been in before. So much that besides a quick dinner out one night (12 min away) and a nice walk around the Mountain Top Arboretum with our dog, we wanted to spend our time at the property. We called it our personal sanctuary spa!! The home: The home style is minimalistic but homey and every single item is top notch quality. There are no shortcuts- the entire place is a work of art. The bedroom and bathroom inspired me to reanalyze my own bedroom style. Thank you for upping the Airbnb game!! Can’t wait to come back to this magical spot! ✨

4.93 out of 5 average rating, 14 reviews

Lake-side Escape

GilbertoRating, 5 stars3 weeks ago

This place was exactly what we expected. Big, spacious, and well maintained. Milot was quick to respond to any questions, very proactive and very helpful and friendly. Would definitely recommend anyone visiting the area to stop by here and check it out for yourself. Top tier vibes & hospitality. 10/10 in my book.

A serene lakeside view features calm waters reflecting the surrounding greenery. Wooden Adirondack chairs and a picnic table are positioned on the grassy shore, with a barbecue grill nearby. A gentle slope leads to a larger area with trees and additional seating, enhancing the tranquil setting.

4.88 out of 5 average rating, 8 reviews

Lake House

DavidRating, 5 stars8 months ago

This place is an absolute gem! We were pleasantly surprised at how much nicer and comfortable it was than even the photos. I strongly recommend this place and Sherri was responsive, friendly, and helpful!