Book Holiday Homes in Penn Yan

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Featured Holiday Homes in Penn Yan

Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Putt Putt Golf on the Wine Trail!

Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Putt Putt Golf on the Wine Trail!

Penn Yan
When you stay at this vacation home in Penn Yan, you'll be on a lake, just steps from Keuka Lake and a 3-minute drive from Arts Center of Yates County.
Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Putt Putt Golf on the Wine Trail!
1-acre lakefront log cabin with dock, 50 ft water frontage, hot tub, & deck

1-acre lakefront log cabin with dock, 50 ft water frontage, hot tub, & deck

Dundee
A stay at this vacation home places you in the heart of Dundee, within a 5-minute drive of Fruit Yard Winery and Glenora Wine Cellars.
1-acre lakefront log cabin with dock, 50 ft water frontage, hot tub, & deck
Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.

Geneva
With a stay at this vacation home in Geneva, you'll be within a 5-minute walk of South Main Street and Smith Center for the Arts.
Historic Geneva Row House near Hobart William Smith Colleges and Linden Street.
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The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK

Penn Yan
Located in Penn Yan, this vacation home is in a rural location, within a 10-minute drive of Keuka Lake Outlet Trail and Arts Center of Yates County.
The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK
Croft Cove | 3 Bed, 2 Bath

Croft Cove | 3 Bed, 2 Bath

Bradford
Located in Bradford, this vacation home is on the waterfront, a 1-minute drive from Lamoka Lake and 6 minutes from Waneta Lake.
Croft Cove | 3 Bed, 2 Bath
Classic country retreat with a game room, bar, expansive outdoor space, & grill

Classic country retreat with a game room, bar, expansive outdoor space, & grill

Penn Yan
With a stay at this vacation home in Penn Yan, you'll be within a 10-minute drive of Keuka Lake and Oliver House Museum.
Classic country retreat with a game room, bar, expansive outdoor space, & grill
Dog-friendly home near downtown, lake, & wine trail with private W/D

Dog-friendly home near downtown, lake, & wine trail with private W/D

Geneva
A stay at this vacation home places you in the heart of Geneva, within a 15-minute walk of South Main Street and Smith Center for the Arts.
Dog-friendly home near downtown, lake, & wine trail with private W/D
Cozy getaway with Keuka Lake views - minutes to wineries

Cozy getaway with Keuka Lake views - minutes to wineries

Hammondsport
With a stay at this vacation home in Hammondsport, you'll be within a 5-minute drive of Keuka Lake and Glenn H. Curtiss Museum.
Cozy getaway with Keuka Lake views - minutes to wineries
Whispering Vines | 4 Bed, 2 Bath

Whispering Vines | 4 Bed, 2 Bath

Keuka Park
Located in Penn Yan, this vacation home is in a rural location, within a 5-minute drive of Keuka Lake and Keuka College.
Whispering Vines | 4 Bed, 2 Bath
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Penn Yan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Penn Yan vacation homes are the perfect way for you to wing it.

Holiday houses in Penn Yan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Penn Yan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Penn Yan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Penn Yan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Penn Yan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Penn Yan Holiday Homes essential information

Accommodation
506 Holiday Homes
Lowest Price
AU$171
Highest Price
AU$209
Popular accommodation
Lakeview w/Pool, Hot Tub, Firepit, Gameroom, Putt Putt Golf on the Wine Trail! , 1-acre lakefront log cabin with dock, 50 ft water frontage, hot tub, & deck, Historic Geneva Row House near Hobart William Smith Colleges and Linden Street., The Farmhouse-Seneca/Keuka-HotTub-WineTrail-1850’s Farmhouse, Classic Red Barn-Big Rooms-Pets OK, Croft Cove | 3 Bed, 2 Bath, Classic country retreat with a game room, bar, expansive outdoor space, & grill, Dog-friendly home near downtown, lake, & wine trail with private W/D, Cozy getaway with Keuka Lake views - minutes to wineries, Whispering Vines | 4 Bed, 2 Bath

Top trending hotels in Penn Yan

Best Western Plus Vineyard Inn & Suites

Best Western Plus Vineyard Inn & Suites

2.5 out of 5
142 Lake St, Penn Yan, NY
Fully refundableReserve now, pay when you stay
The price is AU$209 per night from 7 May to 8 May
AU$209
per night
7 May - 8 May
With a stay at Best Western Plus Vineyard Inn & Suites, you'll be centrally located in Penn Yan, within a 5-minute drive of Keuka Lake and Arts Center of Yates ...
Best Western Plus Vineyard Inn & Suites
Hampton Inn Penn Yan

Hampton Inn Penn Yan

2.5 out of 5
110 Mace Street, Penn Yan, NY
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 28 May to 29 May
AU$171
per night
28 May - 29 May
When you stay at Hampton Inn Penn Yan in Penn Yan, you'll be in a state park, just steps from Keuka Lake and a 2-minute drive from Arts Center of Yates ...
Hampton Inn Penn Yan
Microtel by Wyndham Penn Yan Finger Lakes Region

Microtel by Wyndham Penn Yan Finger Lakes Region

3 out of 5
124 Elm St, Penn Yan, NY
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 5 May to 6 May
AU$188
per night
5 May - 6 May
A stay at Microtel by Wyndham Penn Yan Finger Lakes Region places you in the heart of Penn Yan, a 1-minute drive from Arts Center of Yates County and 7 minutes ...
Microtel by Wyndham Penn Yan Finger Lakes Region
Save an average of 15% on thousands of hotels when you're signed in
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake

Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake

PennYan
With a stay at this cabin in Penn Yan, you'll be on a lake, within a 15-minute drive of Keuka Lake and The Windmill Farm & Craft Market.
Cozy, rustic cabin with beautiful views, privacy, and 1 mile from Keuka Lake
Don't see what you're looking for?
See all available properties in Penn Yan
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.