Holiday houses in Watkins Glen

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.

FLX 3- Lake View Wine Country Tiny Cabin

Nestled up on a hill overlooking Seneca Lake, watch the sunset while laying in bed or from your own patio with a fire crackling. We are local hosts and will make sure you have an unforgettable stay! Everything you could want to do in the Finger Lakes will be at your fingertips. Wineries galore, two even just next door, multiple breweries nearby, minutes to the lake, 15 minutes to downtown Watkins Glen, 10 minutes to hiking trails at the national forest, or stay in, relax, and enjoy the view!!

Falcon Nest - Treehouse Secluded in Private Forest

A Treehouse. Reconnect with nature at this unforgettable escape. Nestled in 28 acres of woods with hiking trails. This unique newly constructed all electric 525 sq foot elevated structure offers a wrap around deck for an ever changing view. King size bed & new technology foam offers complete comfort in separate climate controlled bedroom. Heated bathroom floor is a “warm” surprise. Optional seasonal outdoor shower for the adventurous. Kitchen lacks nothing tucked conveniently in the great room.

Stunning 2Bed 1 1/2 Bath Luxury Vacation Apartment

Here it is! Everything you could ask for in a Luxury Vacation Apartment just one block from Seneca Lake in beautiful downtown Watkins Glen, NY. No amenity was spared with the building of this new 2-bedroom 1-1/2 bath apartment as everything was completed with meticulous attention to detail. Enjoy everything that we have to offer as you are just steps away from many dining, shopping & entertainment options. Located above 29 NEAT Whiskey Bar is every bourbon, cocktail & martini lover's dream!

Hillside Cozy Cabin

Experience a cozy cabin in a country setting with stary nights and wildlife. This 480 sq.ft. cabin will be fully stocked with amenities and more! Smart TV and a electric fireplace for extra coziness. A covered porch to enjoy those summer stormy days/nights. You will also have a firepit, chairs and a propane grill. Only a few miles away from local wineries, breweries, hiking trails, restaurants and Seneca Lake with water activities. Check out our other listing! *CABIN HOSTS UP TO 2 GUESTS!*

1800s Post Office Turned Luxury Couples Getaway

Welcome to 1800 House, a post office turned modern vintage oasis, minutes from the Finger Lakes wine trail. With wide-plank floors, vintage art, a newly renovated chef's kitchen, this second floor home brims with romance and soul. Perfect for a couples getaway or vacation with friends, guests can relax in the clawfoot tub, sleep soundly in the plush, hotel-style bed, and explore the Finger Lakes wine trail. Experience old-world charm with modern luxury in this truly one-of-a-kind listing.

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.

Adventure Awaits A-Frame

Nestled in the forest surround yourself with nature in this cozy A-frame cabin. Enjoy a digital detox in an off grid forest setting (no electricity,wifi,cell) only minutes away from all that the Finger Lakes has to offer. You are close to amazing hiking trails, waterfalls and water sports on Seneca lake, as well as, countless wineries, breweries, and distilleries. This cabin can accommodate 2 adults easily with the a real full-size bed complete with linens. PLEASE READ “Other Details”

Watkins Glen House walking distance to State Park

The property is in walking distance to the Watkins Glen State Park. It has 3 bedrooms each with a king bed and 2 full bathrooms. The house has 1 smart tv and cable and WiFi internet. The kitchen is stocked with cookware, bakeware, dinnerware, silverware, and drinking glasses. Guests can use the stove/oven, microwave, fridge, coffeemaker, toaster, and dishwasher. Dishwasher detergent is provided as well as garbage bags. Please respect the no pets policy.

Wine, Waterfalls & Sunsets from your Bed!

Watch golden sunsets over the mountains—without ever leaving your bed. This romantic, cozy cabin is designed for slowing down and soaking in the view. Couples love our large bedside window as it bring the outdoors in, making every sunset feel like a private show just for you. While it feels secluded and peaceful, you’re just minutes from wineries, waterfalls, and everything the Finger Lakes has to offer.

Serene Tiny House at Osmote Wine

Unwind in this stylish, eco-conscious tiny container home nestled right on the grounds of Osmote Winery, overlooking the stunning waters of Seneca Lake. Whether you're here to sip wine, explore the Finger Lakes, or simply relax in nature, this unique retreat offers a peaceful and memorable escape. Brand new in 2025. No families displaced for short term rental. Insta photos @stayatosmote for more pics

Elegant Historic Flat Iron Building Apt. 3

This is a gorgeous PRIVATE Loft style 2 bed, 2 bath guest apartment located in an historic downtown building in the heart of the Finger Lakes Wine Country. Less than 10 minutes from Watkins Glen International Racetrack & about 7 blocks from the Watkins Glen State Park! Be a part of a local community by staying right downtown and experience all that the Finger Lakes and Watkins Glen have to offer.