Holiday rentals in Hammondsport

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.

Studio Apt in The Pillar House

Take it easy at this unique and tranquil getaway. Just a couple blocks from the village square in Hammondsport. Directly next door to brand new “Service Sration FLX” coffee shop. Voted "Coolest Small Town in America" by readers of Budget Travel, Hammondsport blends fun outdoor activities (like paddleboarding, fishing, boating), breathtaking scenery, award-winning wines and craft beverages, excellent food, and the chance to settle in and experience the best of lake life for yourself.

Updated LakeFRONT Home, Dock, Kayaks, Wine Trail

-Keuka Lakefront -20 wineries within 20 min -5 min drive to Hammondsport: Tons of Shopping, Bars, Restaurants ****Voted "Coolest Small Town in America"*** -Flat Lake Entry, walk right into one of cleanest lakes in the country -Swim/Fish/Kayak right from the house -Fire table, grill by lake -Kayaks included -Newly remodeled & professionally decorated -Sip wine w/ your toes in the water -Dock your boats here -Enjoy views of Wineries -5 min drive to public Beach -All the amenities of home

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.

Pleasant Valley Farmhouse

This recently remodeled farm house is located in Pleasant Valley, 5 minutes from downtown Hammondsport and Keuka lake. Originally built in 1920, this house now boasts a brand new open concept kitchen with high end utilities, up dated bathrooms with built in tile showers, three bedrooms, a dedicated laundry room, outdoor patio with picnic table and a fire pit. The property is secluded and private offering a quiet and relaxing atmosphere for your Keuka lake get away.

Cozy Cottage in the village of Hammondsport

Escape to this newly renovated 2 bedroom 2 bath home, just an 8-minute stroll to the heart of Hammondsport. Sip your morning coffee on the porch and enjoy the morning sun and the charm of the hills of Pleasant Valley. After a day of exploring the Finger Lakes' area, soak your cares away in the hot tub or relax in front of the outside gas fireplace. This home is ideal for a single couple or two couples seeking a refreshing getaway.

The Gulf Stream House Unit 12

The Gulf Stream House is located just steps away from beautiful Keuka Lake! Enjoy all that the village of Hammondsport has to offer- restaurants, local shops and public parks, all within walking distance. Unit 12 is located on the second floor and has it's own private balcony with views of Keuka Lake!

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.

Hammondsport Hideaway

Excellent location in Hammondsport, voted the coolest small town in America! Walk to restaurants, shops and to Keuka lake! Close to local wineries and breweries yet tucked away for a cozy stay in our beautifully decorated space perfect for two!