Photo by Matthew Jay

Penn Yan holiday rentals

We found 828 holiday rentals — enter your dates for availability

Select from 151 homes, 54 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.

Find spaces that suit your style

  • 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)
  • Hazlitt 1852 Vineyards (13.8 mi / 22.2 km)
  • Ventosa Vineyards (14.8 mi / 23.9 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)
  • Sampson State Park (9.1 mi / 14.7 km)
  • Keuka Lake (12.5 mi / 20 km)
  • Canandaigua Lake (15.2 mi / 24.4 km)
  • Seneca Lake State Park (15.8 mi / 25.4 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 home accommodation in Penn Yan?
Houses are the most popular type of holiday home in Penn Yan, according to our data. Even if you have something else in mind, Stayz 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 home 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 home 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 Stayz 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 homes in Penn Yan?
Yes, there are. You can pick from 14 holiday homes that cater to pets in Penn Yan. Plenty of our pet-friendly holiday homes 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 Stayz.
What are popular home amenities in Penn Yan?
Some of the most popular home 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, Stayz holiday properties have the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday homes 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 homes 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 homes in Penn Yan?
Yes, you can pick from three one-bedroom homes 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 homes 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 homes with air conditioning in Penn Yan?
Penn Yan has 13 holiday homes where you’ll be able to chill out in air-conditioned comfort. To find a property on Stayz 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 home in Penn Yan?
You’ll need to check with the Penn Yan holiday property you’re looking at on Stayz as the minimum age varies. However, it’s typically 16, 18 or 21.
How long can I rent a holiday home in Penn Yan for?
The amount of time you can stay in a Penn Yan holiday home 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 Stayz holiday homes may also offer weekly or monthly discounts, so you can stay longer for less money.

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