Our other sites
Get A Free World Heritage Guide »
SeatGuru
Family Vacation Critic
Cruise Critic
BookingBuddy
We recommend:
We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox. Mac: Safari.

Penn Yan Vacation Rentals

Hotels (4)

B&Bs / Inns (10)

Specialty Lodging (1)

Vacation Rentals (89)

The safest rental experience online

Rent from verified owners and managers, and read reviews before you book.

Find out what to expect »

In partnership with:

Get listed!

Add your property »

New and Featured
Piece of Paradise, Keuka Park
Piece of Paradise
    Price: €209/night €767 - €2,087/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 1
    • Contact Manager
Oak Hill Cabin, Keuka Park
Oak Hill Cabin
    Price: €105/night €488 - €941/week
  • Bedrooms: 3, sleeps 6
  • Bathrooms: 1
    • Contact Manager
Roff's Point, Keuka Park
Roff's Point
    Price: €1,045 - €2,017/week
  • Bedrooms: 4, sleeps 8
  • Bathrooms: 2
    • Contact Manager
Crooked Lake Lodge, Keuka Park
Crooked Lake Lodge
    Price: €348/night €1,394 - €3,136/week
  • Bedrooms: 4, sleeps 12
  • Bathrooms: 4
    • Contact Manager
Keuka Pines Bungalow B, Keuka Park
Keuka Pines Bungalow B
    Price: €91 - €108/night €303 - €571/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
Evening Splendor, Keuka Park
Evening Splendor
    Price: €105/night €523 - €1,150/week
  • Bedrooms: 3, sleeps 8
  • Bathrooms: 1
    • Contact Manager
Maya's Palace, Keuka Park
Maya's Palace
    Price: €1,045 - €2,439/week
  • Bedrooms: 4, sleeps 12
  • Bathrooms: 3
    • Contact Manager
Pleasant View Getaway, Keuka Park
Pleasant View Getaway
    Price: €105/night €453 - €836/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
Keuka Pines Bungalow C, Keuka Park
Keuka Pines Bungalow C
    Price: €91 - €108/night €303 - €571/week
  • Bedrooms: 2, sleeps 6
  • Bathrooms: 1
    • Contact Manager
Lake Stone, Keuka Park
Lake Stone
    Price: €157 - €174/night €693 - €2,021/week
  • Bedrooms: 4, sleeps 10
  • Bathrooms: 3
    • Contact Manager

Search Penn Yan Vacation Rentals


Advanced Search

Vacation rentals you can trust

[ Price / nt ] [ Price / wk ] [ Price / mo ] [ Bedrooms ]

There are no vacation rentals within Penn Yan, Finger Lakes, New York. We broadened your search to include all rentals within 5 miles.

The Tree House, Keuka Park
The Tree House
Contact Manager
Nightly rate from
€209
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 10
Bathrooms: 2
Tucked in the woods, this spectacular custom-built log home is located on Keuka's beautiful West Bluff Drive. The spacious, nearly-new home features a ...
  • Nightly
    €209 - €244
  • Weekly
    €833 - €2,056
  • Monthly
    --
Three Sisters, Keuka Park
Three Sisters
Contact Manager
Nightly rate from
€209
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 12
Bathrooms: 3
Paradise Found! Extraordinary setting for this 5 bedroom lakefront home. Private drive off the main road, featuring landscaped grounds and extensive lawn ...
  • Nightly
    €209
  • Weekly
    €1,045 - €2,613
  • Monthly
    --
Keuka on the Rise, Keuka Park
Keuka on the Rise
Contact Manager
Nightly rate from
€157
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Wonderful views of the lake and bluff abound from within this unique lakefront cottage. Enjoy spectacular vistas from every room and fromprivate balconies ...
  • Nightly
    €157
  • Weekly
    €627 - €1,324
  • Monthly
    --
Sailfish Cottage, Keuka Park
Sailfish Cottage
Contact Manager
Nightly rate from
€139
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 8
Bathrooms: 2
Quality lake living at an affordable price, and close to area attractions! Charming lake cottage, completely updated with quality furnishings. Exterior entry ...
  • Nightly
    €139
  • Weekly
    €610 - €1,220
  • Monthly
    --
Waterfront Chateau, Keuka Park
Waterfront Chateau
Contact Manager
Nightly rate from
€174
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 7
Bathrooms: 2
Relax in this bright, recently redecorated lakeside home. Located in walking distance to the Switzerland Inn, which has excellent food and live music on the ...
  • Nightly
    €174
  • Weekly
    €624 - €1,530
  • Monthly
    --
Windsong, Keuka Park
Windsong
Contact Manager
Nightly rate from
€122
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Memories are made in this attractive, 3 bedroom colonial style cottage! With excellent views from the covered porches off the front of the house or the ...
  • Nightly
    €122
  • Weekly
    €523 - €1,115
  • Monthly
    --
Serendipity, Keuka Park
Serendipity
Contact Manager
Nightly rate from
€226
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 10
Bathrooms: 3
Policy: Smoking not allowed Check-In: 4:00pm (Saturday) Check-Out: 10:00am
  • Nightly
    €226
  • Weekly
    €1,045 - €2,578
  • Monthly
    --
Riesling Retreat, Keuka Park
Riesling Retreat
Contact Manager
Nightly rate from
€296
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 3
"The Riesling Retreat" is a chalet style home with a Nantucket flair situated in the middle of the Bluff, with fantastic views of the lake and vineyards. It ...
  • Nightly
    €296 - €314
  • Weekly
    €1,185 - €2,439
  • Monthly
    --
Nature's Retreat, Keuka Park
Nature's Retreat
Contact Manager
Nightly rate from
€139
Management: Professional
Property: Rental Home
Bedrooms: 4, sleeps 8
Bathrooms: 2
This charming, two story lakeside cottage sits right at the water's edge. Located on a quiet road, on Keuka's beautiful Bluff, this property offers fantastic ...
  • Nightly
    €139 - €174
  • Weekly
    €523 - €1,620
  • Monthly
    --
Chateau Merlot, Keuka Park
Chateau Merlot
Contact Manager
Nightly rate from
€122
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 9
Bathrooms: 2
Picture yourself is this charming A-Frame lakeside cottage, located just a few miles from the village of Hammondsport! With over 130 feet of lakefront, it ...
  • Nightly
    €122 - €174
  • Weekly
    €557 - €1,672
  • Monthly
    --
Victorian on the Lake, Keuka Park
Victorian on the Lake
Contact Manager
Nightly rate from
€261
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Completely remodeled turn of the century lake home! With all the original architecture still in place, this home has tons of appeal to vacationing guests. A ...
  • Nightly
    €261
  • Weekly
    €1,324 - €2,021
  • Monthly
    --
Hale Moku, Keuka Park
Hale Moku
Contact Manager
Nightly rate from
€122
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 7
Bathrooms: 1
The name 'Hale Moku'is Hawaiian for "home of the sailor that has returned from the sea". Named in honor of the legacy owner, Perry W. Johnson, Jr. Lt. Cmdr, ...
  • Nightly
    €122
  • Weekly
    €627 - €1,254
  • Monthly
    --
Lakewood Landing, Keuka Park
Lakewood Landing
Contact Manager
Nightly rate from
€122
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Bathrooms: 2
This beautiful Cape Cod has just become available for rental. With three spacious bedrooms and two full bathrooms, the cottage provides exceptional comfort ...
  • Nightly
    €122
  • Weekly
    €557 - €1,045
  • Monthly
    --
Pinewood, Keuka Park
Pinewood
Contact Manager
Management: Professional
Property: Rental Home
Bedrooms: 2, sleeps 6
Bathrooms: 1
Wooded privacy can be enjoyed from this charming 2 bedroom cottage located near the end of East Bluff Drive. The paved driveway ends right next to the ...
  • Nightly
    --
  • Weekly
    €1,220
  • Monthly
    --
Glory Days, Keuka Park
Glory Days
Contact Manager
Nightly rate from
€244
Management: Professional
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 4
Please check back soon for property description! Policy: Smoking not allowed Check-In: 4:00pm (Friday) Check-Out: 10:00am
  • Nightly
    €244
  • Weekly
    €1,394 - €2,300
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns