Family-friendly holiday rentals in Hammondsport

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.

A Wise Getaway / Farm Cottage Near Keuka Lake

Welcome to A Wise Getaway Amish-Built 800 Sq Ft Cottage on 50-Acre Farm No Cleaning Fee Upfront - All-In Pricing *One-time $50 pet fee A peaceful retreat for couples, families & your four-legged friends 2 miles from Keuka Lake & minutes to the Village of Hammondsport, NY Minutes from wineries, breweries, NYS hunting land & Waneta / Lamoka Lakes ♿ Handicap accessible 🐾 $50 pet fee 🔥 Fire pit 📡 Wi-Fi 🍔 BBQ grill Top 5% rated Airbnb in region 20–30 mins to Watkins Glen, Penn Yan & Corning

Heard It View The Grapevine

Walking distance to Dr. Frank's Winery, Barrelhouse 6 Distillery, & Divided Sky Winery. A 6 minute or less drive to Point of the Bluff Winery & Concert venue, Keuka Brewing, Krooked Tusker Distillery, Steuben Brewing, Heron Hill Winery & Bully Hill Winery. Panoramic clear views boast from this hilltop hideaway. Perfect family vacation or couples getaway spot for the ultimate Finger Lakes retreat. Fiber Optic internet at the house. Rare for this area - better speeds and more reliable service.

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

Pulteney Pleasure

Beautiful renovated apartment. Fully equipped kitchen for those who love to cook. Located on Keuka Wine Trail, on the west side of Keuka Lake, 3 min. from Point of Bluff Concert Venue. Close to Dr. Konstantin Frank Winery, 1886 Tasting Room, 3 distilleries and Steuben Brewing Co. 10 min. to Hammondsport and 15 min. to Penn Yan. Host is next door and offers farm to table dining options for guests. EV charger new in 2024. Also Pulteney Garden Escape for second option.

Finger Lakes with a lake view, walk to Wineries!

Keuka Lake view cottage located half way between Hammondsport and Penn Yan on the East side of the lake. This is a year round guest house that was rebuilt in 2019-2020. It has a beautiful lake view from inside the house and from the front porch, we do not provide direct lake access. Location to launch your boat 1/2 mile away, walk to 2 wineries & 1 distillery, 1/2 mile to The Switzerland Inn & Keg & Barrell. We are also close to Watkins Glen and Seneca Lake.

FLX 4-Lake View Wine Country Tiny Cabin

Nestled up on a hill with Seneca Lake peaking through the trees. 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!!

Pet Friendly Keuka Wagon

Stay in a One-of-a-Kind Covered Wagon Travel the Keuka Lake Wine Trail and experience the Finger Lakes in a whole new way! Our Covered Wagon blends Yellowstone charm with modern comforts, including a queen bed, pull-out futon, full bathroom with shower, TV, fast Wi-Fi, heat, A/C. Enjoy complimentary coffee, and we don’t charge a pet fee—bring your furry friends along! Have questions? Message us anytime—we’re happy to help!

Riesling Retreat - Waterfront Cottage, Lamoka Lake

Riesling Retreat is situated on scenic Lamoka Lake, in NY’s Finger Lakes Region, between Keuka and Seneca lakes. Our cottage is professionally cleaned after each visit and boasts an expansive covered porch, full kitchen with gas stove and island for cooking, manicured lawn with fire pit, dock, and launch for the kayaks or canoe. It is central to Watkins Glen, Hammondsport, and more than 250 wineries; you can’t go wrong!

Bed n' fix your own damn Breakfast

Come and sit on the Veranda with a glass of wine and some cheese. You will be one block from restaurants and shops and 2 blocks from a public beach for swimming and fishing on Beautiful Keuka Lake. Many wineries, breweries and distilleries within close driving distance. There are also a handful seasonal restaurants right on the water. This is a place to slow down and recharge.

Family Fun in the Village

Enjoy your own little home away from home in downtown Hammondsport. This sweet home is recently remodeled and located just a short walk from downtown Hammondsport and Keuka Lake. We are also just a short drive from some of the best wineries and breweries in the area!

Cottage on the Square in the Heart of Hammondsport

The Cottage offers the best of both worlds – the Village Square with fine shops, pubs & restaurants – and Keuka Lake for boating, fishing & natural beauty . . . all within a short walk! And for wine enthusiasts, a better location could not be found.