Holiday houses in Hammondsport

4.97 out of 5 average rating, 516 reviews

Apartment in Penn Yan

Crows nest lake view flat

Crows Nest is located on the Keuka Lake wine trail. It is next to Red Jacket Park and Morgan Marine on one side, Seasons on Keuka Lake on the other. Very close to Penn Yan/Yates County Airport and between the Main Deck restaurant and Route 54. The property is NOT water front. Keuka Lake is accessible thru Red Jacket Park and visible from the property, but not directly on the water. There is a sidewalk from the property to town for Guests who prefer to walk, approximately 1 mile to Village center

Guesthouse in Hammondsport

4.95 out of 5 average rating, 107 reviews

Waterfront Cottage with moorage on Keuka Lake

Charming cottage on the waterfront with a beautiful view of the lake. Direct access that’s mere steps to the water with large dock/mooring for swimming/watersport fun. Fully furnished with a great kitchen, outdoor grill and a comfy queen sized bed. It's only 5 miles to the town square with lots of cute shops & quaint restaurants. Close to a variety of wineries, craft breweries & hiking/biking trails. A short drive to the Glenn H. Curtiss Museum and just over the hill from Watkins Glenn raceway!

4.97 out of 5 average rating, 250 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.

Guesthouse in Hammondsport

4.89 out of 5 average rating, 335 reviews

A Wise Getaway AirBnB

Simple Amish-Built Cottage on 50-Acre Farm near Keuka Lake 800 sq ft cozy, Pet-Friendly escape just 2 miles from Keuka Lake & minutes to Village of Hammondsport, NY & award winning wineries & breweries. Handicap accessible Includes Wi-Fi, fire pit, bbq grill Premium DIRECTV (HBO, Starz + Various Sports Packages) 5 mins to Waneta / Lamoka Lakes & NYS hunting land. 20-30 mins to Watkins Glen, Penn Yan & Corning. Not the Ritz—just peaceful country living Top 5% rated Airbnb in our region

4.93 out of 5 average rating, 258 reviews

Home in Keuka Park

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!

4.99 out of 5 average rating, 108 reviews

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

4.93 out of 5 average rating, 293 reviews

Apartment in Pulteney

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.

Tiny home in Hammondsport

4.97 out of 5 average rating, 199 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!

Guest suite in Hammondsport

4.88 out of 5 average rating, 186 reviews

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.

4.89 out of 5 average rating, 137 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.

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Other great holiday rentals in Hammondsport

Cabin in Hammondsport

4.88 out of 5 average rating, 50 reviews

Lake View with Balcony- Private 2 bedroom chalet

AbigailRating, 5 stars3 weeks ago

Great remote spot about 10 minutes from downtown Hanmondsport. Stacey was very proactive in communicating with us. There was a considerable amount of rain prior to our stay so she worked very hard to make sure the driveway was cleared for us to drive through. (The driveway is wooded leading up to the house.) It’s a cozy spot, great for just a few people. The view was great on the back deck and made for relaxing starts to the morning.

4.94 out of 5 average rating, 90 reviews

Cabin in Bath

The Cabin

SusanRating, 5 stars1 week ago

Mitchell’s cabin is better than describe. As a fellow five star super host Mitchell does an amazing job. My wife and I had a small family issue that we needed to take care of and Mitchell was very understanding with us. I cannot say enough about the place and the host you want to stay here.

5 out of 5 average rating, 56 reviews

Farm stay in Bath

Mountain Rose Horse Farm - Loft Studio

ArtRating, 5 stars5 days ago

I spent a week on the farm. Perfect place to relax and ride a horse. Pictures are great but seeing it in person is better. The barn was fully equipped and clean. Rachel is an excellent host. Don't pass it up.

4.97 out of 5 average rating, 91 reviews

Tiny home in Wayne

Keuka Lake-Bound “Tiny House”

PaulRating, 5 stars1 week ago

If you're looking to get away and find a nice little place to relax and unwind, this place was perfect. While private and peaceful, it's not very far from splendid views or excellent dining!

5 out of 5 average rating, 9 reviews

Cabin in Hammondsport

Pinot In The Pines - Adorable Private Cottage

TiffanyRating, 5 stars2 months ago

This cottage is such a gem! Cozy, welcoming, and thoughtfully designed, it was the perfect home base for our trip. It is private and peaceful while still being conveniently close to town (Hammondsport) and lots of wineries (Keuka Lake/Seneca Lake). The little touches—vintage record player, some fun DVDs, and a fire pit, for an evening under the stars—made our stay extra special. The hosts were so kind, and very quick to communicate. They were also very helpful and provided wonderful recommendations for wineries, restaurants, and local services that helped us make the most of the region. Will absolutely be staying here again!

4.93 out of 5 average rating, 15 reviews

Private Lakefront Cottage on Keuka Lake

JolieRating, 5 stars7 months ago

This Airbnb was the perfect fall getaway! We visited the lake to soak in the autumn vibes, and this spot exceeded our expectations. There was plenty of room for our group of five, and the host’s recommendations made our trip even better. While the area is known for summer fun, I think fall might be the best time to visit. We had an amazing time exploring the charming shops, cozy restaurants, and stunning waterfront spots, plus the nearby vineyards are a must-see. Can’t wait to return next year when the leaves are changing again—absolutely loved our stay!

4.91 out of 5 average rating, 120 reviews

Family Fun in the Village

Mary KayRating, 5 stars2 weeks ago

We were extremely delighted with our stay at Ashlee’s home. Pleasantly surprised to find deliciously fresh baked cookies, a chilled bottle of Weis wine, fresh coffee beans and the best tasting organic eggs – such generous and thoughtful touches to welcome us. The house was so clean, well appointed to and cozy which made our stay unforgettable. We highly recommend and can not wait to return next year! Thank you.