Holiday rentals in Hammondsport

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Top-rated holiday rentals in Hammondsport

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Cottage in Hammondsport
4.91 out of 5 average rating, 410 reviews

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

Top guest favourite
A spacious chalet is nestled on a verdant hilltop, surrounded by a variety of trees. The wide deck extends from the building, providing an inviting outdoor space. Fluffy clouds float above a vibrant blue sky, enhancing the natural beauty of the scenic vineyard landscape.
Chalet in Prattsburgh
4.99 out of 5 average rating, 106 reviews

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.

Top guest favourite
A charming lakeside house is positioned above the water, surrounded by lush greenery. A spacious deck extends over the lake, providing views through large windows. The exterior is painted in soft yellow, complemented by a blue awning, enhancing the cozy lakeside ambiance.
Guest house in Keuka Park
4.99 out of 5 average rating, 374 reviews

Keuka Beach House - Glamping at its best!

My place is right on the lake and great for summer activities. The deck hangs out over the water overlooking the beach and dock. Outdoor opportunities include your own hiking trail on five acres of land behind the house, cycling, swimming, kayaking and canoeing. It's a great place for couples, solo adventurers, and pets who like to swim. Currently, New York State charges 8% sales tax and Yates County charges 4% Occupancy Tax which is added to the amount you pay when booking the space. Sorry.

Top guest favourite
A spacious great room featuring gleaming hardwood floors and large picture windows that provide panoramic views of the surrounding hills. A kitchen island stands prominently in the center, accompanied by a dining table with multiple chairs, creating an inviting space for gathering.
Home in Hammondsport
4.97 out of 5 average rating, 286 reviews

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.

Top guest favourite
A tranquil lakeside view during fall showcases vibrant foliage, with trees in shades of orange, red, and yellow. Crisp leaves blanket the ground, while the calm water reflects the colorful landscape. A wooden dock is visible in the background, inviting relaxation by the lake.
Home in Keuka Park
4.94 out of 5 average rating, 290 reviews

Mutual Fun Keuka Memories

If you are going to just hang out, do it at this beautiful setting on Keuka Lake. Child-Friendly. Wonderful swimming area! Scenic drives around the vineyards. Spacious, comfortable home along a very quiet road. Cozy All-Season getaway! Enjoy your own private beach and dock. Swim/float/kayak in pristine waters. Walk along the lake. Stargaze. Campfires on the shore. Wintertime retreat. Brand new leather sofa, chair and ottoman. Nice, warm fireplace. Snuggle inside and let it snow!

Top guest favourite
Home in Hammondsport
4.97 out of 5 average rating, 347 reviews

Hammy on a Rye I Hammondsport Village

Enjoy a relaxing stay in this beautifully remodeled Hammondsport home, just 1½ blocks from the Village Square and 4½ blocks from Keuka Lake. The home features a king bedroom, queen bedroom, 1½ baths, laundry, Smart TVs, Wi-Fi, private outdoor seating, and off-street parking. Walk to restaurants, shops, parks, and the lake. Minutes from award-winning wineries, breweries, museums, and Keuka Water Sports. Dog-friendly and ideal for couples, families, and Finger Lakes adventures.

Guest favourite
A welcome sign for Hammondsport is framed by vibrant autumn foliage. The sign features bold lettering against a backdrop of seasonal plants and landscaping, with a clear blue sky overhead. The setting emphasizes the natural beauty of the area.
Home in Hammondsport
4.91 out of 5 average rating, 105 reviews

Private and plentiful in Hammondsport NY

Hammondsport NY Easy walking just outside village. Spacious full downstairs. 1 queen bedroom and 1 queen pull out sofa full bathroom, kitchen, livingroom and seasonal front room . Walking distance to beautiful Keuka Lake beaches, parks , boat/jet ski rental, restaurants, bars and many attractions. 5 minute drive to several Wineries,Breweries, Antiques, Glen H.Curtiss Museum , Boat Museum and Fingerlakes trail. Beautiful senic overlooks along both sides of the lake.

Top guest favourite
A welcoming front porch features two blue chairs and a small white table, set against a gray exterior. The yellow front door adds a pop of color, while potted flowers and a decorative planter enhance the inviting appearance. Steps lead up to the porch, providing access.
Cottage in Hammondsport
4.98 out of 5 average rating, 112 reviews

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.

Top guest favourite
A scenic lakeside view features a wooden dock extending into Keuka Lake, surrounded by gentle waves and distant hills. The image highlights the clear blue sky and partly cloudy backdrop, offering a tranquil atmosphere. A small structure is visible in the foreground, providing access to the lake.
Tiny home in Hammondsport
4.97 out of 5 average rating, 216 reviews

Shalestone Landing (Lakeside Tiny House)

As the name suggests, Shalestone Landing sits nestled in at the bottom of our home vineyard, atop layers and layers of hidden shale.....perfect for growing grapes! This quaint and comfortable tiny house is located on the west side of Keuka Lake offering lakeside views of gorgeous Keuka Lake. Shalestone Landing is perfect for a couple or small family (up to 4) looking to get away!

Top guest favourite
A two-story home features a blue exterior with white trim and large front windows allowing for ample light. A welcoming entrance is enhanced by a set of black railings leading up a concrete staircase. Surrounding greenery adds a natural touch to the property.
Home in Hammondsport
4.92 out of 5 average rating, 156 reviews

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!

Guest favourite
A charming two-story cottage with a light siding exterior is surrounded by lush greenery. The inviting front porch features large windows for natural light, while the upper balcony adds a cozy dimension. A well-maintained garden borders the pathway leading to the entrance.
Home in Hammondsport
4.88 out of 5 average rating, 147 reviews

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.

Top guest favourite
A spacious loft-style living area features vaulted wood-paneled ceilings and ample natural light. Comfortable seating is arranged around a central coffee table, complemented by a large area rug. A kitchenette is visible in the background, along with a dining space, enhancing the open layout.
Barn in Hammondsport
5 out of 5 average rating, 116 reviews

The Barn at Graystones

The Barn at Graystones is a private spacious loft-style rental with a tennis-pickleball court and brand new amenities. Enjoy a relaxing stay with lake views, conveniently located in the heart of the Finger Lakes region. A perfect getaway for two.

Popular amenities for Hammondsport holiday rentals

When is the best time to visit Hammondsport?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Hammondsport?

    Hammondsport has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Hammondsport?

    Experience the best of Hammondsport with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Hammondsport?

    Four-legged friends are welcome in Hammondsport. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Hammondsport?

    Yes! Work meets play with ease at over 10 vacation rentals in Hammondsport featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Hammondsport have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Hammondsport. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Hammondsport have a kitchen?

    Absolutely! We offer over 10 apartment rentals with a kitchen in Hammondsport. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Hammondsport have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Hammondsport. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Hammondsport have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Hammondsport. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Hammondsport

  • Total holiday rentals

    Explore 40 holiday rentals in Hammondsport

  • Nightly prices starting at

    Hammondsport holiday rentals start at £52 per night before taxes and fees

  • Verified guest reviews

    Over 2,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Hammondsport holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Hammondsport rentals

  • 4.9 Average rating

    Hammondsport stays are highly rated by guests – averaging 4.9 out of 5!

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