Vacation rentals with lake access in Sleepy Hollow Lake, Greene County, New York

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

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Guest favorite

Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.

Home in Athens

4.95 out of 5 average rating, 132 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, kayaks, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, or work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking, art galleries, antique shops, and cultural centers.

Guest favorite

A clear lake displays calm waters reflecting the surrounding greenery and mountains. Smooth stones line the water's edge, while trees provide a natural frame. A lakeside home is visible in the background, integrating seamlessly with the tranquil landscape.

Home in Chichester

4.97 out of 5 average rating, 150 reviews

Stunning Pvte Lakehouse•Swim•Hike•Mntn Views•F/pit

Wake up to stunning mountain views and enjoy a SWIM in your OWN PRIVATE LAKE (only you!) sparkling clear lake surrounded by 5 secluded ac. of the stunning Catskill Mountains . Lie out on the swim dock, row the boat, enjoy coffee or grill on the wrap-around deck, cook in the gourmet kitchen, or simply relax by the fire (wood-burning fireplace inside as well as a lakeside FIREPIT). Minutes to swim holes, hiking, breweries & the town of Phoenicia. You need never leave! This is the ULTIMATE getaway.

Top guest favorite

Home in Ancram

4.99 out of 5 average rating, 179 reviews

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

All size Dogs & Cats Welcome *Outside backyard is large and surrounded by trees with Firepit, Hammock & Volleyball Net +Watercraft available - Kayaks/Rowboat Swim Platform Indoor Wood Burning Fireplace Fully stocked kitchen and toiletries 10-15 minutes to Bash Bish Falls/Catamount Aerial Park/Ski/Snowboard/Tubing 25-30 minutes to Berkshires Shoe shoeing +November-April: watercraft not available, also weather dependent *Only one neighbor, is to the left, separated by trees and bushes

Top guest favorite

The exterior of the lakefront home showcases a vibrant blue facade, framed by well-maintained green lawns and leafy trees. A spacious deck is visible, along with multiple large windows that enhance the inviting appearance of the property.

Home in Valatie

5 out of 5 average rating, 111 reviews

Escape to Lakefront Leisure—Amazing views!

Welcome to this beautiful lake-front home on Kinderhook Lake, NY. Totally rebuilt in 2018, this home is designed to maximize the incredible view of the lake. Cool and sunny in the summer, and warm and cozy in the winter. Come and relax on Lake Kinderhook!! Brand new 6 person hot tub. Relax and unwind while 45 jets massage your muscles, summer or winter! Ever sit in the steaming hot water while snow falls around you? Upgraded 400/100 internet for work/school! About 2 hrs from New York City!

Guest favorite

An aerial view showcases a serene lake bordered by lush greenery and trees, with the elegant cottage nestled among them. A private dock extends into the calm waters, reflecting the surrounding nature. The expansive landscape emphasizes the cottage's tranquil, waterfront location.

Home in Great Barrington

4.96 out of 5 average rating, 166 reviews

Elegant Year-Round Lakeside Retreat with AC

The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.

Top guest favorite

A charming cottage is nestled among trees, featuring a spacious deck adorned with colorful umbrellas. Steps lead down to a lawn bordered by vibrant flowers and a dock with seating. Kayaks are positioned nearby, and the tranquil lake reflects the surrounding greenery.

Cottage in Valatie

4.99 out of 5 average rating, 141 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

Welcome to our paradise-where time slows down and memories are made. It's the perfect retreat for relaxing, kayaking, swimming, hiking, biking, and so much more. -Sip your coffee on the decks while enjoying lake wildlife -Grab a kayak or paddleboard and explore the 8 miles of shoreline -Catch the sunset, then end the day sharing stories around the starlit firepit An ideal base for exploring restaurants, breweries, wineries, galleries, historical sites, trails, farm stores, and orchards.

Guest favorite

Home in Athens

4.92 out of 5 average rating, 118 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.

Guest favorite

A scenic view from a wooden deck showcases a tranquil lake surrounded by greenery. Bright, leafy trees frame the image as the calm water reflects the sky. Cozy seating is positioned on the deck, inviting relaxation in this serene outdoor space.

Chalet in Hunter

4.98 out of 5 average rating, 152 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

Every room in this lakefront modern cabin is designed to make you feel embraced by nature, boasting breathtaking views of the serene lake and lush forest. Perched on a hillside of the famous Hunter Mountain, just a short walk from the ski slopes in winter and mere steps from the lake in summer. With unlimited hiking options and top-notch golf courses just minutes away, our location truly has it all for those seeking adventure and relaxation or a memorable venue for reunions and gatherings.

Guest favorite

A lakefront home is visible at the end of a private dock, surrounded by lush greenery and open fields. The water's edge is marked by tall grasses, with clear blue skies above and hints of distant structures along the shoreline.

Home in Copake

4.95 out of 5 average rating, 20 reviews

Lakeside Haven

4 bedroom Lakefront Home with private dock for paddle boarding, kayaking, swimming, hiking trails and golf course. 4 ski mountains. Vineyards, breweries, distilleries, restaurants! Fire pit, 2 level deck. Gas grill and 2 kitchenware stocked kitchens! Open floor plan with spectacular lake views. Master bedroom with bath. Two queen bedrooms, hall bath. Lower level bedroom with two sets of bunkbeds. TV and game table for family fun nights! Laundry room. Garage Mudroom and outdoor ski rack.

Guest favorite

An aerial view captures a tranquil lakefront property surrounded by lush greenery. A sandy beach area is visible, featuring lounge chairs and a small dock extending into the water. The home is nestled among trees, providing a serene retreat.

Chalet in Athens

4.89 out of 5 average rating, 102 reviews

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.

Guest favorite

Home in Averill Park

4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

Guest favorite

An aerial view displays the surrounding area, highlighting a private dock adjacent to the lake, with well-spaced homes and lush greenery. A clear pathway leads from the house to the dock, emphasizing the convenience of lakeside access.

Cottage in Copake Lake

4.85 out of 5 average rating, 74 reviews

Cozy Retreat on Copake Lake in our Charming Home

Copake Lake, a 410-acre gem in Columbia County, NY, offers a diverse community and abundant activities just two hours from NYC. With a mix of local and second-home residents, this glacial lake boasts public golf courses, a thriving Conservation Society, and a range of housing options. Activities include year-round lake adventures, and the central location allows easy access to Hudson, Great Barrington, and ski resorts.