Holiday houses 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.

Lakeview Crossing Vacation Rental

Lakeview Crossing is an 1800s farmhouse that has been completely renovated. The house sits on a hill overlooking Keuka Lake with vineyards below. Located along the wine trail, guests are short trips away from many local wineries, breweries, a distillery and antique shops. The town of Hammondsport is 6 miles away and has 2 local beaches for swimming and lake activity, restaurants, gift shops, antique shops, groceries, ect. There is a large deck overlooking the lake and the vineyards.

"Spacious Serenity: Keuka Hillside Retreat"

Discover serenity in this charming 2-story home on Keuka's eastern hillside, nestled between Hammondsport and Penn Yan. With an open floor plan, a hot tub, propane fire table, and a spacious deck, it's your ideal Finger Lakes retreat. Set on 29 acres, enjoy proximity to boat launches, wineries, distilleries, and delightful restaurants just 1-2 miles away. Consider additional ground floor space for an even more indulgent stay. Your perfect escape to relaxation and natural beauty awaits!

Keuka West Lakehouse

Enjoy your own private getaway on the west shore of beautiful Keuka Lake in our newly renovated Lakehouse. Experience picturesque morning sunrises and the moon rising over the bluff at night from our expansive deck just a few feet from the shoreline and your own private dock and beach. We are just minutes away from some of the best wineries, breweries, and restaurants in the area. Only 45 minutes from Bristol Mountain Ski Resort, we are a great location for winter activities as well!

Waneta Lakeside Cottage

Right on the water with lots of space and fresh air this new and charming cottage is situated in the heart of the Finger Lakes on the east side of Waneta Lake. Ideal for 1 to 2 couples, a girls weekend getaway or families up to 4. There are 2 bedrooms, an open fully equipped kitchen, a sitting area and bathroom with walk-in shower. Dine and relax on the over-sized covered deck overlooking the lake. A stairway from the deck provides access to a private beach with 4 kayaks.

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

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.

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!

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.