Penn Yan holiday rentals

We found 905 holiday rentals — enter your dates for availability
Select from 156 homes, 57 cottages and other holiday rentals in Penn Yan to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as Wi-Fi and a hot tub. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Penn Yan

Showing deals for:29 Jan - 5 Feb

Interior
Exceptional
(12 reviews)

Finger Lakes Lodge overlooking Keuka Lake with 1st floor master bed & bath!

Pulteney

8% off
S$6,875
for 7 nights, 1 cabin
S$982 per night
includes taxes & fees
Finger Lakes Lodge overlooking Keuka Lake with 1st floor master bed & bath!
Exterior
Exceptional
(14 reviews)

Private, Rustic, Quiet, Quirky! Welcome to O'Cottage! 150 feet of lake frontage

Penn Yan

6% off
S$10,254
for 7 nights, 1 cottage
S$1,465 per night
includes taxes & fees
Private, Rustic, Quiet, Quirky! Welcome to O'Cottage! 150 feet of lake frontage
Property grounds
Exceptional
(49 reviews)

Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23

Penn Yan

7% off
S$4,471
for 7 nights, 1 home
S$639 per night
includes taxes & fees
Panoramic Keuka Lake Views And Breathtaking Sunsets! Save Aug 16-23
Brand new beautiful upperboat house deck with grill and lots of seating
Exceptional
(18 reviews)

Wine trail lakefront luxury on Seneca Lake

Geneva

7% off
S$3,314
for 7 nights, 1 home
S$473 per night
includes taxes & fees
Wine trail lakefront luxury on Seneca Lake
Interior
Exceptional
(155 reviews)

Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes

Branchport

8% off
S$996
for 7 nights, 1 cabin
S$142 per night
includes taxes & fees
Newly Renovated Rustic Cabin w/WiFi in the Heart of the Finger Lakes
Southside porch
Exceptional
(5 reviews)

Charming 4-bedroom house with WiFi and AC in Branchport

Branchport

8% off
S$8,215
for 7 nights, 1 home
S$1,174 per night
includes taxes & fees
Charming 4-bedroom house with WiFi and AC in Branchport
Terrace/patio
Exceptional
(14 reviews)

Bluebird Cabin - Brand New Cozy Log Cabin on 5-Wooded Acres / Pet-Friendly!

Dundee

7% off
S$2,381
for 7 nights, 1 cabin
S$340 per night
includes taxes & fees
Bluebird Cabin - Brand New Cozy Log Cabin on 5-Wooded Acres / Pet-Friendly!
Spacious living room
Exceptional
(202 reviews)

Friends And Family Farmhouse

Penn Yan

8% off
S$5,289
for 7 nights, 1 home
S$756 per night
includes taxes & fees
Friends And Family Farmhouse
Outdoor dining
Exceptional
(16 reviews)

Beautiful Seneca Lake Chalet with stunning lake and Pond views

Penn Yan

7% off
S$2,487
for 7 nights, 1 chalet
S$355 per night
includes taxes & fees
Beautiful Seneca Lake Chalet with stunning lake and Pond views
A charming rental home located in the heart of the Finger Lakes region.
Exceptional
(36 reviews)

Finger Lakes House has private Pool, Fire Pit & Extra Amenities in Hammondsport

Hammondsport

7% off
S$3,149
for 7 nights, 1 home
S$450 per night
includes taxes & fees
Finger Lakes House has private Pool, Fire Pit & Extra Amenities in Hammondsport
Living area
Exceptional
(10 reviews)

The Cabin At Keuka Lake-Great Views overlooking the Lake!

Penn Yan

8% off
S$4,061
for 7 nights, 1 home
S$580 per night
includes taxes & fees
The Cabin At Keuka Lake-Great Views overlooking the Lake!
New view under Cabana
Exceptional
(72 reviews)

Birchwood Cottage, 220ft of Lake Beach-Fully flat lot -Private Driveway

Branchport

7% off
S$4,177
for 7 nights, 1 home
S$597 per night
includes taxes & fees
Birchwood Cottage, 220ft of Lake Beach-Fully flat lot -Private Driveway
Newly remodeled kitchen 2022 with beautiful solid surface countertops
Exceptional
(116 reviews)

Dreaming a View - Tranquil Retreat on Seneca Lake - Sleeps 12

Dresden

8% off
S$13,380
for 7 nights, 1 home
S$1,911 per night
includes taxes & fees
Dreaming a View - Tranquil Retreat on Seneca Lake - Sleeps 12
Owners share 2 kayaks,peddle boat & row boat w/guests at 2 rental properties
Exceptional
(100 reviews)

Cozy Cottage with 45' Lake Frontage and Kayaks

Lodi

17% off
S$17,375
for 7 nights, 1 cottage
S$2,482 per night
includes taxes & fees
Cozy Cottage with 45' Lake Frontage and Kayaks
Outdoor dining
Exceptional
(198 reviews)

Serenity Zen House on Seneca Lake - Pet Friendly

Penn Yan

7% off
S$3,399
for 7 nights, 1 home
S$486 per night
includes taxes & fees
Serenity Zen House on Seneca Lake - Pet Friendly
Room
Exceptional
(16 reviews)

Rock Stream Estate | Wine trail with a hot tub surrounded by nature

Rock Stream

8% off
S$21,845
for 7 nights, 1 home
S$3,121 per night
includes taxes & fees
Rock Stream Estate | Wine trail with a hot tub surrounded by nature
Private kitchen
Exceptional
(6 reviews)

Finger Lakes wine country Keuka Lake!

Hammondsport

7% off
S$2,235
for 7 nights, 1 home
S$319 per night
includes taxes & fees
Finger Lakes wine country Keuka Lake!
Property grounds
Wonderful
(119 reviews)

Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch

Dundee

8% off
S$11,910
for 7 nights, 1 home
S$1,701 per night
includes taxes & fees
Large Lakefront Reunion And Retreat Home With a large lawn and wrap around porch
Beach front
Exceptional
(119 reviews)

Idyllic Lakeside Victorian Farmhouse

Rock Stream

7% off
S$8,017
for 7 nights, 1 home
S$1,145 per night
includes taxes & fees
Idyllic Lakeside Victorian Farmhouse
Living area
Exceptional
(473 reviews)

A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake

Penn Yan

8% off
S$2,392
for 7 nights, 1 cabin
S$342 per night
includes taxes & fees
A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake
We have outdoor seating (an umbrella is available for use) as well as a fire pit
Wonderful
(14 reviews)

Cottage Retreat in the Heart of the Finger Lakes

Ovid

7% off
S$1,227
for 7 nights, 1 cottage
S$175 per night
includes taxes & fees
Cottage Retreat in the Heart of the Finger Lakes
View from the living room
Exceptional
(171 reviews)

Chalet overlooking Keuka Lake in the heart of Wine Country

Penn Yan

14% off
S$1,384
for 7 nights, 1 chalet
S$198 per night
includes taxes & fees
Chalet overlooking Keuka Lake in the heart of Wine Country
Dining
Exceptional
(12 reviews)

3-bedroom waterfront home in fabulous Geneva with AC, WiFi. Enjoy your stay

Geneva

7% off
S$3,409
for 7 nights, 1 home
S$487 per night
includes taxes & fees
3-bedroom waterfront home in fabulous Geneva with AC, WiFi. Enjoy your stay
open layout living room
Exceptional
(22 reviews)

Lakefront vacation with stunning views & sunken deck hot-tub along the winetrail

Dundee

7% off
S$3,348
for 7 nights, 1 home
S$478 per night
includes taxes & fees
Lakefront vacation with stunning views & sunken deck hot-tub along the winetrail
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The friendly area of Penn Yan awaits your stay

Enjoy the wineries and other features of Penn Yan. Revered for its lake, hiking and restaurants, this city is both welcoming and walkable. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Penn Yan

Are you searching for attractions to see in the city? Venture out of your holiday home and experience everything that Penn Yan has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Fox Run Vineyards (6.4 mi / 10.2 km)
  • Wagner Vineyards (11.7 mi / 18.9 km)
  • Three Brothers Wineries and Estates (12.9 mi / 20.7 km)
  • Glenora Wine Cellars (12.9 mi / 20.8 km)
  • Ravines Wine Cellars on Seneca Lake (13 mi / 20.8 km)
  • Hazlitt 1852 Vineyards (13.8 mi / 22.2 km)

Exploring the natural features in Penn Yan

Whether you're an active traveller or just want to take in the scenery, Penn Yan is a great place to spend some time outside. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Keuka Lake Outlet Trail (2.6 mi / 4.2 km)
  • Keuka Lake State Park (6.8 mi / 10.9 km)
  • Seneca Lake (7.6 mi / 12.3 km)
  • Sampson State Park (9.1 mi / 14.7 km)
  • Keuka Lake (12.5 mi / 20 km)
  • Canandaigua Lake (15.2 mi / 24.4 km)

Transport to and around Penn Yan

The nearest airport is in Ithaca, NY (ITH-Tompkins Regional), located 32.7 mi (52.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Elmira, NY (ELM-Elmira - Corning Regional), which is 35.3 mi (56.9 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Penn Yan?
Houses are the most popular type of holiday rental in Penn Yan, according to our data. Even if you have something else in mind, Vrbo has holiday homes in loads of sizes and shapes. Compare our options to find your perfect fit.
How much does it cost to rent a holiday rental in Penn Yan?
The average price for a holiday home in Penn Yan can vary based on factors like length of stay, property type and season. Whether you're looking for a sprawling house with room for friends and family or a cosy cottage just enough for two, just enter your travel dates to see stays with exceptional value.
How much does it cost to rent a beach house in Penn Yan?
The average price for a holiday rental close to the beach in Penn Yan will depend on when you're going and the size and style of property you want. Find prices easily on Vrbo by entering your dates of travel. Then use the handy filters to select the number of bedrooms and amenities important to you, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday rentals in Penn Yan?
Yes, there are. You can pick from 14 holiday rentals that cater to pets in Penn Yan. Plenty of our pet-friendly holiday rentals come with a garden for your furry pal to play around in, special dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.
What are popular rental amenities in Penn Yan?
Some of the most popular rental amenities people look for in Penn Yan are nearby museums, a garden and a water view. Whether you're holidaying with pals, family or even pets, Vrbo holiday properties have the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday rentals in Penn Yan?
Penn Yan has four holiday homes that can host 10 or more guests. These stays come with the space and privacy you need to enjoy good times with friends and family.
Are there holiday rentals in Penn Yan that welcome kids?
Gather your whole crew for the adventure of a lifetime in Penn Yan at one of our 14 family-friendly holiday properties. A lot of these stays feature amenities that are perfect for trips with the kids, such as laundries, extra bedrooms and entertainment areas. Just check the "Properties good for families" filter and decide on your favourite.
What are the top attractions for families in Penn Yan?
Keep the kids busy at these leading family-friendly attractions in Penn Yan:
  • Keuka Lake State Park
  • Keuka Lake Outlet Trail
  • Arts Centre of Yates County
Are there one-bedroom holiday rentals in Penn Yan?
Yes, you can pick from three one-bedroom rentals in Penn Yan. Whether you're on the lookout for a cosy chalet or a condo, our one-bedroom properties are great if you don't require a lot of space. One of the best things about having your own pad? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday rentals in Penn Yan?
Gather your besties and enjoy a relaxing escape in one of the four two-bedroom holiday homes Penn Yan has to offer.
How can I find holiday rentals with air conditioning in Penn Yan?
Penn Yan has 13 holiday rentals where you'll be able to chill out in air-conditioned comfort. To find a property on Vrbo that has this perk, enter your preferred travel dates and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday rental in Penn Yan?
You'll need to check with the Penn Yan holiday property you're looking at on Vrbo as the minimum age varies. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental in Penn Yan for?
The amount of time you can stay in a Penn Yan holiday rental for depends on each property. Just put in your dates of travel to view available options offering longer term stays. They include all the things you need to make your extended trip more convenient and comfortable, such as kitchens and yards. Some Vrbo holiday rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

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