Holiday rentals with a pool in Steuben County

Sky House- private sanctuary in the clouds

Float among the clouds at Sky House, where a crackling wood stove and sweeping views of Keuka Lake will leave you feeling at peace and in awe. Sky House is perfect for special celebrations, romantic getaways, personal creative retreats, or a WFH change of scenery. We are located on the Bluff with 20 acres over looking the west side of the lake. Just five minutes from Keuka Lake State Park! We’re so excited to share this slice of heaven with you! *Four wheel drive needed for winter months*

Sleeps 6 | Lake Access | Near Wineries | Pet Frien

Charming 2 bedroom/2 bathroom pet friendly (with fee) home in the heart of the Finger Lakes, set on Mill Pond off Lamoka Lake. Just minutes from wineries, Keuka and Seneca Lakes, and Watkins Glen. Enjoy stunning lake views, an open-concept living area, bunk room, and private upstairs suite. Relax on the spacious deck or in the pool, or go for a paddle and enjoy the eagles flying across the lake. Perfect for a peaceful getaway with easy access to outdoor adventures and local attractions.

Adorable Walkable Paradise w/ Deck & Pool!

Seasonal Pool Access | National Historic Landmark | Scenic Mountain Views | Close to Wineries & Breweries Situated in the historic town of Hammondsport, this luxuriously restored vacation rental puts local attractions and Keuka Lake adventures within easy reach! Sip your morning coffee on the patio, then gear up for a day on the water or take a trip to Watkins Glen State Park. As evening approaches, return to 'Coachman’s Quarters' for a BBQ on the deck. Sip, explore, and stay awhile.

Hornby Heaven WITH POOL & Hot Tub

This property is ready for you to come make memories! A ranch house surrounded by 150 acres of private trails for you to explore. This home features a private, heated indoor pool as well as a hot tub, sauna and much more. Your family will be close to everything when you stay at our centrally-located home. Located conveniently in between all that our area has to offer! • 10 minutes to downtown Corning • 20 minutes to Watkins Glen • 20 minutes to Elmira Corning Regional Airport

Country Artist's Loft

This artist's loft space is an apartment above the barn shaped garage. The space offers the peaceful sounds of the Amish buggies clip clopping by, beautiful views of rolling farm land, and paths through flower gardens. An actual artist lives in the main house and her art decorates the walls of the loft. (She offers painting class Experiences!) A perfect spot for time of retreat and refreshing but not too far from attractions like museums, Amish markets, lakes and hiking areas.

Tranquil Airstream Nature Escape

Escape to the Finger Lakes and experience the charm of Airstream living! Our Airstream Bambi is a peaceful retreat designed for relaxation, adventure, and reconnecting with nature. Spend your days sipping coffee by the fire pit, enjoying your own pool exclusively for Airstream guests, exploring local wineries, or stargazing beneath the trees. This unique stay offers the perfect blend of comfort, simplicity, and outdoor living. Perfect for nature lovers and pet-friendly too!

Modern Lakeside Villa with Pool and Hot Tub

Introducing Esprit Bleu, a newly built and designed lakeside villa vacation home in the heart of Keuka Lake Finger Lakes wine country, situated on 20 private acres of uncut meadow. 5 day minimum July/Aug The home features 3 bedrooms downstairs and an open floor plan upstairs with views of the adjacent vineyard and just a 5 minute drive to Keuka Lake. Pet friendly An inground heated pool May-Oct and hot tub highlight this home that stuns all year. Pets permitted.

Lakeview House near Wineries & Wedding Venue

Wake up to your own front-row seat to the ever-changing vista on Keuka Lake — your view, 24/7. The Petalstone House is a boutique-style home hotel in Hammondsport’s Finger Lakes wine country, welcoming up to 8 guests. All main living areas are on one floor — comfortable for elderly guests and convenient for families. Between Bully Hill and Heron Hill Wineries, minutes from Living Roots, and across from the Manor House Estate — ideal for wedding guests.

Norris View

Norris View is a one‑of‑a‑kind hillside retreat designed to give you space, comfort, and complete relaxation. Built directly into the hill, this thoughtfully designed home naturally stays cool during the summer—enjoy fresh air through open windows with gently circulating fans, even on warm days. Whether you’re looking to spend sunny days lounging by the pool, exploring nearby trails, or enjoying cozy nights filled with laughter and relaxation.

Finger Lakes Home w/ Private Pool & Lake Views!

Private Acreage | 8 Mi to Champlin Beach (Keuka Lake) | Fire Pit Immerse yourself in an unparalleled escape at this 3-bedroom, 2-bath vacation rental situated in the heart of Hammondsport wine country! This vacation rental features an updated interior complete with everything you need for a perfect getaway. Voted ‘Coolest Small Town in America,’ Hammondsport offers incredible scenery and wines, year-round outdoor fun, and holiday markets!

Keuka Glory

Welcome to Keuka Glory! Enjoy some time on the deck and take a swim while enjoying Keuka’s splendor. Check out the new Living Roots tasting room across the road or take a trip into the village and enjoy a fabulous meal at The Village Tavern Restaurant. Take a walk over to Crooked Lake Ice Cream Company for dessert. For that farm-to-table experience enjoy a dinner at The Park Inn.

Keuka Glory! Spectacular views of Keuka Lake!

Welcome to Keuka Glory! Enjoy some time on the deck and take a swim while enjoying Keuka’s splendor. Check out the new Living Roots tasting room across the road or take a trip into the village and enjoy a fabulous meal at The Village Tavern Restaurant. Take a walk over to Crooked Lake Ice Cream Company for dessert. For that farm-to-table experience enjoy a dinner at The Park Inn.