Holiday houses in Wheeler

Timber View At Timber Trails

Escape to the countryside at the charming, “Timber View.” Surrounded by wineries & scenic beauty, this country retreat offers a peaceful getaway for those seeking to disconnect & rejuvenate. Wake up to the sounds of nature, enjoy your morning coffee on the porch, & spend your days exploring the Finger Lakes region with activities like hiking, visiting local farmers' markets, or simply enjoying the tranquility of rural life. In the evenings, gather around the fire pit for stories and stargazing.

The Lakeview Chalet: Cozy & Chic, Hot Tub, Games

Relax & unwind to a backdrop of Canandaigua Lake! This rustic chalet on a private setting has that cozy cabin feel with modern styling and luxurious amenities including a gas stove fireplace, hot tub, nostalgic games, library, outdoor fire pit & more! Amenities Include: Hot Tub with Lake View Gas Stove/Fireplace Fire Pit BBQ Grill Foosball Table Board Games A/C in Loft BR Heat Parking: 4 Spaces High-Speed Internet/Wifi Smart TV/Cable Library Desk Alexa Speaker Telescope STR Permit #: 2023-0073

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.

Secluded Cabin, Hot Tub, Fire Pit, Pets, Grill

Escape to the Black Birch Cabin – a stylish, romantic hideaway designed for couples. Tucked away in the heart of the woods, this cozy cabin offers ultimate seclusion w/ a private hot tub, a crackling fire pit, and serene forest surroundings. Perfect for unwinding together, whether stargazing by the fire, playing board games, enjoying the peaceful ambiance, or simply reconnecting. The Black Birch cabin invites you to relax, recharge, and create unforgettable memories in a truly magical setting.

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.

Modern Villa Vineyard Stay on Historic Property

Enjoy a beautiful new small home in the heart of the Fingerlakes- minutes from downtown Watkins Glen! This home - Villa Sage - is located on a historic property that was once a winery. The villa sits on a small vineyard and offers beautiful indoor and outdoor spaces. Inside offers high ceilings, a huge shower with a rainfall showerhead, a Japanese joinery bed, plush linens, a well appointed kitchen, a convertible sofa, & much more. Outside offers a private firepit/lounge space & vineyard.

Hammy on a Rye 2 Hammondsport NY

There have been professional photos done by the Airbnb photographer, and they are finally here! This is the 2nd Hammy on a Rye right next door to the original Hammy on a Rye started almost 4 yrs ago. This is similar in size and layout as the other home. It has two king-size bedrooms, 2 full baths, a kitchen, a dining room, a living room, laundry, and central air. There is also plenty of off-street parking available. We are putting together the gas firepit and seating now

A-Frame on Keuka Lake

This house has a suite with a king bed, mini-kitchen, and a full bath (shower). There is a second bedroom with a queen bed and a separate bath (tub/shower). There is a large living room, a full eat-in kitchen and an outdoor grill. Extra seating including a dining table and picnic table is available on the deck overlooking the lake. There is a separate rental unit (Keuka Beach House) along the lake that shares the beach and dock, just a one-minute walk down the hill.

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.

Junior's Suite

Enjoy a bright and inviting stay in this charming upstairs unit of the historic Carriage House at J.S. Hubbs Guest House. Junior’s Suite features two bedrooms, one bathroom (with tub), and a spacious living area — perfect for families or friends exploring Keuka Lake and Hammondsport’s Village Square, just steps away. With Roku TVs, comfortable furnishings, and off-street parking, it’s a welcoming home base filled with character, comfort, and a touch of family history.

Tiny Vineyard Mirror House with Sauna & Hot Tub

Introducing Le Petit Miroir, a mirrored tiny house in the heart of Finger Lakes Wine Country on 20 scenic private acres. House features a sauna, hot tub, queen size bed, cozy living space and chic shower. Dine al fresco outside under the stars with bbq grill and fire pit. The mirror house interiors are not visible from the outside during day, only from inside can you view out to adjacent vineyard. 5 min drive to Keuka Lake. 4 day minimum July/August

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.