Penn Yan Vacation Rentals

Compare 13 vacation rentals.
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USA > New York > Penn Yan

Make Penn Yan your next getaway

The historic village of Penn Yan is home to wineries, a quiet way of life, and of course the beauty of the Finger Lakes—from falls to gorges to sparkling waters. If you’re ready to experience this special place for yourself, our Penn Yan vacation rentals may be just what you’re looking for.

Explore Penn Yan house rentals, cabins, cottages, and more

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House rentals

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Cabins

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Cottages

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Popular amenities for Penn Yan vacation rentals

Popular
Dog-friendly Hot tub Internet
Keuka Lake Sunrise
3 Bedroom | 2 Bath | Sleeps 7

Keuka Lake Sunrise - Penn Yan, NY

$269 avg / night
(excludes fees and taxes)
Cedar Barn Sanctuary
1 Bedroom | 1 Bath | Sleeps 4

Cedar Barn Sanctuary - Penn Yan, NY

$223 avg / night
(excludes fees and taxes)
4.75 (4)
Windmill Family Home
3 Bedroom | 2.5 Bath | Sleeps 6

Windmill Family Home - Penn Yan, NY

$207 avg / night
(excludes fees and taxes)
4.82 (11)
Marina Vista
9 Bedroom | 4 Bath | Sleeps 24

Marina Vista - Penn Yan, NY

$867 avg / night
(excludes fees and taxes)
4.21 (28)
Keuka Lake Dockside Retreat
3 Bedroom | 2.5 Bath | Sleeps 8

Keuka Lake Dockside Retreat - Penn Yan, NY

$354 avg / night
(excludes fees and taxes)

View 8 more homes

Recent Penn Yan guest reviews

Throughout the years, My husband and I have stayed at many vacation homes… To this home we are returning guests because this one in particular stands out for many reasons. Although there may be some minor imperfections that are basic cosmetic things, none of those things are a bother to us due to the overall cozy feel and relaxing environment. Both my husband, myself and our kids can truly relax in this home and not feel on edge like we might mess something up like some vacation homes have made us feel in the past. Definitely not a walking on egg shells type of place. It has all the basic cookware that you need for those who like to stay in and cook, but there’s a perfect balance of good restaurants in very close vicinity as well as grocery stores. The downtown is cute and relaxing, and there are just so many nearby lakes, it’s great! One that stands out in particular is Indian pine park because there is also a playground there. I love the horse and buggies that are all around and we especially love visiting Keuka Restaurant, as well as Shtayburne Farm Creamery with the kids to get fresh ice cream and cheese and visit the baby calves. This is a dog friendly home so we are grateful for that as well, being as though we like to take our pups with us when we vacation. Not to mention the lovely walking trail right across the non busy road. I recommend this place to the down to earth people who love nature and enjoy relaxing.
Deb T. | May 2025
Beautiful place to stay gave us a centered place to stay as we traveled visiting wineries and other attractions
Charles W. | May 2025
Clean, comfortable and spacious
Harmony M. | May 2025
Penn Yan vacation rental FAQ

Yes, 11 of our Penn Yan homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 31 of our Penn Yan vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Penn Yan vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Penn Yan team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Penn Yan, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
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Professional cleaning

Where is Penn Yan, NY?

The Finger Lakes are made up of 11 long, narrow lakes in beautiful upstate New York. Penn Yan is nestled on the north shores of Keuka Lake, and is centrally located in the heart of the entire region. You’ll be about 50 miles from Ithaca where, if you choose, you can explore the city’s shops, museums, and the historic campus at Cornell University.

Things to do near Penn Yan, NY

Folks come to Penn Yan in search of a quiet getaway in a small town, surrounded by beautiful outdoors—and that’s exactly what they receive. Of course, there are the stunning, pristine waters of Keuka Lake, offering everything from kayaking to trout fishing to watching vivid sunsets over the water.

About 30 minutes from our Penn Yan vacation homes is Watkins Glen State Park, where a trail meanders past 19 cascading waterfalls—you can even walk beneath some of them. The stone bridges appear to be made from the rocks themselves, and in the autumn the surrounding trees are alight with color.

After your morning hike, stop by the Penn Yan Diner for a hearty stack of the best pancakes in town. You’ll love the retro feel of this cozy space, with only 10 tables plus counter seating. If it’s a Saturday, pop by the Windmill Farm and Craft Market to explore 50 unique vendors selling baked goods, crafts, and more. It’s open between April and December and often features live music and dance performances. If you just can’t get enough northeastern flair, Wagers Cider Mill is a great spot for a sweet treat—apple cider and apple cider donuts, to be exact.

No Finger Lakes vacation would be complete without exploring the local vineyards. The area is peppered with them, each offering their own unique vibe and atmosphere. From the trendy Three Brothers—wine slushie, anyone?—to the high-end Belhurst Castle, you won’t be short of options. The tasting room at Keuka Spring Vineyards is just minutes from our Penn Yan vacation rentals, for an easy trip.

The Finger Lakes region has so much to offer in the way of relaxation and unwinding. Treat yourself to a tranquil getaway—browse our selection of Penn Yan vacation homes.