Penn Yan, New York

Vacation Rentals in Penn Yan, New York

Discover 121 vacation rental properties in Penn Yan. From 1 to 11 bedrooms. Average $454/night. 100% have pools.

121 verified listings Book securely on VRBO Prices updated March 2026

121 properties available

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

2 beds 1 bath
PoolA/CWiFiBalcony
$240/night
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While Away Cottage

While Away Cottage

3 beds 2 baths
PoolA/CWiFiBalcony
$292/night
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NEW Seneca Lake View Chalet with Pond

NEW Seneca Lake View Chalet with Pond

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK

Anthony Beach-Seneca-Waterfront-Hot Tub-Wine Trail-Big Deck, Recently Updated-New Dock-Pets OK

2 beds 1 bath
PoolA/CWiFiBalcony
$363/night
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Rustic Ridge Log Cabin

Rustic Ridge Log Cabin

1 bath
PoolA/CWiFiBalcony
$121/night
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Cedar Lane Cabin | 3 Bed, 1 Bath

Cedar Lane Cabin | 3 Bed, 1 Bath

3 beds 1 bath
PoolA/CWiFiBalcony
$177/night
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Pine Grove Cabin

Pine Grove Cabin

1 bed 1 bath
PoolA/CWiFiBalcony
$79/night
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Cozy new England style cottage Right on Wine and Beer Trail

Cozy new England style cottage Right on Wine and Beer Trail

2 beds 1 bath
PoolA/CWiFiBalcony
$250/night
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Dog-friendly home with washer/dryer, outdoor dining & grill - walk to town

Dog-friendly home with washer/dryer, outdoor dining & grill - walk to town

3 beds 1 bath
PoolA/CWiFiBalcony
$191/night
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Penn Yan House Rental - Close to Wineries!

Penn Yan House Rental - Close to Wineries!

2 beds 1 bath
PoolA/CWiFiBalcony
$97/night
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Serenity Aloft House - Now with Town Water

Serenity Aloft House - Now with Town Water

2 beds 2 baths
PoolA/CWiFiBalcony
$429/night
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Cozy Bungalow right on the Lake wine and brewery trail.

Cozy Bungalow right on the Lake wine and brewery trail.

1 bed 1 bath
PoolA/CWiFiBalcony
$196/night
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Dog-friendly home with fenced backyard & W/D - lake trails across the street

Dog-friendly home with fenced backyard & W/D - lake trails across the street

3 beds 1 bath
PoolA/CWiFiBalcony
$178/night
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Sampson House | 3 Bed, 1.5 Bath

Sampson House | 3 Bed, 1.5 Bath

3 beds 1 bath
PoolA/CWiFiBalcony
$192/night
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The Heart Of The Wine Country! Sip wine, take a dip, relax and enjoy

The Heart Of The Wine Country! Sip wine, take a dip, relax and enjoy

3 beds 1 bath
PoolA/CWiFiBalcony
$216/night
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Apt in the Heart of Penn Yan < 1 Mile to Lake!

Apt in the Heart of Penn Yan < 1 Mile to Lake!

1 bed 1 bath
PoolA/CWiFiBalcony
$201/night
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Quiet And Cozy Cabin With 165 Ft. Private Beach On Seneca Lake. LGBTQ+ friendly

Quiet And Cozy Cabin With 165 Ft. Private Beach On Seneca Lake. LGBTQ+ friendly

1 bed 1 bath
PoolA/CWiFiBalcony
$498/night
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Beautiful Views, Sunrises, Pet Friendly, Comfortable!

Beautiful Views, Sunrises, Pet Friendly, Comfortable!

2 beds 2 baths
PoolA/CWiFiBalcony
$396/night
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Wine Trail Covered Wagon

Wine Trail Covered Wagon

1 bed 1 bath
PoolA/CWiFiBalcony
$198/night
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Sheridan House Studio | 0 Bed, 1 Bath

Sheridan House Studio | 0 Bed, 1 Bath

1 bath
PoolA/CWiFiBalcony
$192/night
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Beautiful house on the lake

Beautiful house on the lake

4 beds 2 baths
PoolA/CWiFiBalcony
$541/night
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Grand Luxury Escape In The Heart Of Finger Lakes Wine Country

Grand Luxury Escape In The Heart Of Finger Lakes Wine Country

3 beds 2 baths
PoolA/CWiFiBalcony
$300/night
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Close to wineries, room for family, lakeview, gourmet kitchen, yard, easy in/out

Close to wineries, room for family, lakeview, gourmet kitchen, yard, easy in/out

4 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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Smith's Lake House, new-build 2021, enjoy that million dollar view

Smith's Lake House, new-build 2021, enjoy that million dollar view

4 beds 2 baths
PoolA/CWiFiBalcony
$610/night
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Waterfront cottage on Keuka Lake near Penn Yan

Waterfront cottage on Keuka Lake near Penn Yan

3 beds 2 baths
PoolA/CWiFiBalcony
$276/night
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located in the heart of downtown Penn Yan New York

located in the heart of downtown Penn Yan New York

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
View Details → Book on VRBO
Penn Yan Vacation Rental: 1 Mi to Keuka Lake!

Penn Yan Vacation Rental: 1 Mi to Keuka Lake!

4 beds 2 baths
PoolA/CWiFiBalcony
$257/night
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Keuka East: Spacious & Comfy

Keuka East: Spacious & Comfy

5 beds 3 baths
PoolA/CWiFiBalcony
$466/night
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Beautiful Keuka Lake Home close to Penn Yan

Beautiful Keuka Lake Home close to Penn Yan

3 beds 3 baths
PoolA/CWiFiBalcony
$541/night
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Crane Cove | 4 Bed, 3 Bath

Crane Cove | 4 Bed, 3 Bath

4 beds 3 baths
PoolA/CWiFiBalcony
$439/night
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WOW! Newly Renovated Cottage on Keuka Lake. Perfect for a Vacation on the Water

WOW! Newly Renovated Cottage on Keuka Lake. Perfect for a Vacation on the Water

4 beds 1 bath
PoolA/CWiFiBalcony
$349/night
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Cozy apartment on Keuka Lake, close to Keuka College, wineries and breweries.

Cozy apartment on Keuka Lake, close to Keuka College, wineries and breweries.

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
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Delightful lakefront house with furnished deck, balcony, and private dock

Delightful lakefront house with furnished deck, balcony, and private dock

4 beds 3 baths
PoolA/CWiFiBalcony
$461/night
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Lake Front Cottage

Lake Front Cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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Our Happy Retreat: "Finger Lakes Reunions on Keuka Lake! Pet Friendly + Hot Tub!"

Our Happy Retreat: "Finger Lakes Reunions on Keuka Lake! Pet Friendly + Hot Tub!"

6 beds 3 baths
PoolA/CWiFiBalcony
$961/night
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Keuka Lake Waterfront Getaway - Finger Lakes/Wine County

Keuka Lake Waterfront Getaway - Finger Lakes/Wine County

3 beds 1 bath
PoolA/CWiFiBalcony
$352/night
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Keuka Lake House - East Side - Sunsets and Gorgeous Views

Keuka Lake House - East Side - Sunsets and Gorgeous Views

2 beds 1 bath
PoolA/CWiFiBalcony
$351/night
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Stunning, Fully-Loaded Home with Private Hot Tub, Pool Table, and Dock

Stunning, Fully-Loaded Home with Private Hot Tub, Pool Table, and Dock

9 beds 4 baths
PoolA/CWiFiBalcony
$712/night
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Panoramic Keuka Lake Views And Breathtaking Sunsets!

Panoramic Keuka Lake Views And Breathtaking Sunsets!

4 beds 2 baths
PoolA/CWiFiBalcony
$643/night
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Majestic lakefront home with private hot tub, dock, grill, beach, fireplaces, AC

Majestic lakefront home with private hot tub, dock, grill, beach, fireplaces, AC

5 beds 4 baths
PoolA/CWiFiBalcony
$781/night
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On Cloud Wine | 5 Bed, 3 Bath

On Cloud Wine | 5 Bed, 3 Bath

5 beds 3 baths
PoolA/CWiFiBalcony
$472/night
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Stunning Keuka Lake House! Kayak, SUP, fish, swim, campfires

Stunning Keuka Lake House! Kayak, SUP, fish, swim, campfires

4 beds 3 baths
PoolA/CWiFiBalcony
$856/night
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At The Lake - 4 Bedroom, 3.5 Bath Contemporary

At The Lake - 4 Bedroom, 3.5 Bath Contemporary

4 beds 2 baths
PoolA/CWiFiBalcony
$664/night
View Details → Book on VRBO
Finger Lakes Keuka Lake Vacation Home 50' off water, 100' Level Beach Frontage

Finger Lakes Keuka Lake Vacation Home 50' off water, 100' Level Beach Frontage

5 beds 2 baths
PoolA/CWiFiBalcony
$561/night
View Details → Book on VRBO
Updated Open Plan - Keuka Lakefront Home 4BR & 157' private beach

Updated Open Plan - Keuka Lakefront Home 4BR & 157' private beach

4 beds 2 baths
PoolA/CWiFiBalcony
$645/night
View Details → Book on VRBO
HUGE DECK! ENJOY the beauty and quaintness of this 3 bedroom and 2 bath cottage

HUGE DECK! ENJOY the beauty and quaintness of this 3 bedroom and 2 bath cottage

3 beds 2 baths
PoolA/CWiFiBalcony
$391/night
View Details → Book on VRBO
Keukation - A Beautiful Lakefront Home.

Keukation - A Beautiful Lakefront Home.

4 beds 2 baths
PoolA/CWiFiBalcony
$611/night
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Bluffing Around: "Family Friendly Lakeside Paradise!"

Bluffing Around: "Family Friendly Lakeside Paradise!"

3 beds 1 bath
PoolA/CWiFiBalcony
$375/night
View Details → Book on VRBO

Showing 48 of 121 properties

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