Vacation rentals in Wheeler

2br Chalet with Hot Tub on a 30+ acre vineyard

Welcome to Whispering Pines, an immaculate 2 bedroom, 1.5 bath chalet on a vineyard overlooking Keuka Lake. Relax on a large, private deck equipped with a year-round hot tub while taking in the beauty of the surrounding vistas. At night, you will be treated to breathtaking panoramas of the celestial bodies above. Located within 10 miles from many wineries, breweries, restaurants, wedding & event venues and local attractions. Truly a unique place to enjoy all that the Finger Lakes has to offer.

Keuka Beach House - Glamping at its best!

My place is right on the lake and great for summer activities. The deck hangs out over the water overlooking the beach and dock. Outdoor opportunities include your own hiking trail on five acres of land behind the house, cycling, swimming, kayaking and canoeing. It's a great place for couples, solo adventurers, and pets who like to swim. Currently, New York State charges 8% sales tax and Yates County charges 4% Occupancy Tax which is added to the amount you pay when booking the space. Sorry.

School House Retreat at Hemlock Ridge Farm

Enjoy stellar sunrises and sunsets, farm fresh food from the Hemlock Ridge Farm Store, featuring organic eggs from our free-range hens, maple syrup, grass fed beef, plus a full stock of organic bulk foods, including your morning coffee beans! There's a firepit and picnic table for an evening bonfire, perfect for watching the sunset and stargazing. Fully equipped kitchen, newly renovated bathroom, washer and dryer. Crisp cotton sheets on antique bedframes welcome you for a restful night!

Peace and Contentment

Forget your worries in this spacious and serene space. Though just minutes from major highways, the country setting is quiet and peaceful. There’s space to run and play, a front porch to enjoy coffee and the sunrise, and a back patio for dining and relaxing. The views are spectacular for seeing whitetail deer, turkeys, and the occasional bear. Located in the heart of the Finger Lakes; Keuka, Seneca, Canandaigua lakes, and Watkins Glen, Letchworth, and Stoney Brook State Parks are close by.

High Ridge Escape

This cozy bungalow features 180-degree views of the entire valley! The renovated cabin is situated on 34-acres, featuring hiking trails, magnificent views, and an abundance of wildlife and nature. The property is off of a private drive, making it the perfect place for a couple or small family to escape the hassles of life. The property also features an outdoor picnic area and firepit. Approximately 15-minutes from Naples (Canandaigua Lake) and 20-minutes from Hammondsport (Keuka Lake).

Hammy on a Rye I Hammondsport Village

Enjoy a relaxing stay in this beautifully remodeled Hammondsport home, just 1½ blocks from the Village Square and 4½ blocks from Keuka Lake. The home features a king bedroom, queen bedroom, 1½ baths, laundry, Smart TVs, Wi-Fi, private outdoor seating, and off-street parking. Walk to restaurants, shops, parks, and the lake. Minutes from award-winning wineries, breweries, museums, and Keuka Water Sports. Dog-friendly and ideal for couples, families, and Finger Lakes adventures.

Family & Dog Friendly Retreat | 2mi to Keuka Lake

Private 3-acre retreat minutes from Hammondsport and Keuka Lake. Perfect for families and dog lovers, featuring a large yard, fire pit (wood included), covered deck, and outdoor games like disc golf and cornhole. Sleeps 5 with a king bedroom, bunk room, and futon. Enjoy a full kitchen, laundry, and dedicated office space. Peaceful and secluded, yet close to wineries, breweries, museums, and the Finger Lakes Trail. 30 minutes to Watkins Glen, Naples, Corning, & Penn Yan.

The Cabin

Experience true relaxation at this updated cabin just up the hill from the beautiful small town of Hammondsport, NY and the head of Keuka Lake. Explore the countless wineries nearby making up the Keuka lake wine trail, along with several breweries and distilleries. Surrounded by picturesque wooded landscape and open fields, enjoy cooking on the grill, over a campfire, or chose one of the unique restaurants in downtown Hammondsport or others nearby.

Finger Lakes Get-Away

This charming getaway offers a perfect blend of comfort, fun, and relaxation making it the ideal spot to reconnect with nature and each other. Featuring a fully equppied kitchen for family-style meals, a game room for a little friendly competition, plus Starlink internet, a private hot tub, and a fire pit. Whether you're looking to stay in or explore the Finger Lakes, this country retreat has everything you need for a memorable stay.

Seasoned Valley Homestead

Nestled in a quiet farming valley, our cozy rustic homestead offers the perfect countryside retreat. Escape the hustle of everyday life and slow down with fresh country air, wide open spaces, and plenty of room to relax. Whether you’re looking for a peaceful getaway or a taste of simple farm living, our homestead is the perfect place to unplug, unwind, and make lasting memories—whether for a weekend or a longer stay.

Cozy 2 bed 2 bath single wide near highway

This clean and cozy single wide trailer has two full bathrooms and two bedrooms. Newly updated throughout with new washer and dryer. Plenty of parking space outside with easy access to the highway in the heart of the Finger Lakes region. New, spacious and private porch off back entrance. Bonus 2000 sq ft building next to trailer with wrestling mats throughout for your use if you like!

Wine Country Farmhouse

Escape to this spacious 3-bedroom home set on a large private lot—perfect for relaxing, playing, or entertaining. Enjoy room to roam inside and out, with comfortable living areas and beautiful open surroundings. Ideal for families, friends, or anyone craving space and tranquility.