Discover a selection of 500 vacation rentals in Penn Yan, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $96 per night, and houses and cabins are popular options for a stay in Penn Yan. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Penn Yan
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Destination guide

The friendly area of Penn Yan awaits your stay

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

Things to do

Sightseeing in and around Penn Yan

Are you hoping to discover things to do while you're in town? Venture out of your vacation home and experience everything that Penn Yan has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Damiani Wine Cellars (16.8 mi / 27 km)
Natural features

Exploring the natural features in Penn Yan

Whether you're looking for adventure or just want to take in the scenery, Penn Yan is a great spot to appreciate mother nature. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
How to get there

Transportation 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 center. If you can't find a flight that works for your travel itinerary, you could also fly into Elmira, NY (ELM-Elmira - Corning Regional), which is 35.3 mi (56.9 km) away.

What are the top vacation rentals in or near Penn Yan?

The heart wants what the heart wants, and right now that's a vacation. Now's the time to pack your suitcase and escape to one of these top vacation rentals in or near Penn Yan:

  • "Quiet And Cozy Cabin With 165 Ft. Private Beach On Seneca Lake. Lgbtq+ Friendly" is a popular choice. Around 7 miles from Penn Yan, it has 1 bedroom and plenty of handy amenities, including coffee and tea making facilities and a beach view.
  • Another appealing choice is "Gorgeous Waterfront Home With Huge Flat Yard", which is around 9 miles from Penn Yan. With 2 bedrooms, nearby museums and a dryer, it has everything you need to keep you happy and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Penn Yan vacation rental for you.

Can I find log cabins to rent in or near Penn Yan?

Whether you're after a basic retreat or a luxurious escape, you'll find an excellent range of log cabins to rent in Penn Yan. Experience a blend of comfort and adventure at one of these options:

  • If you'd like to be able to go golf or kayaking while staying in Penn Yan, "A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake" in Town of Jerusalem will be a terrific choice.
  • Alternatively, get your vacation on at "Lakeside Log Cabin In The Heart Of The Finger Lakes". Try some kayaking or cycling or simply put your feet up at this Penn Yan property.

What are the top-rated vacation rentals for weekend getaways in or near Penn Yan?

If you've been busier than an ant at a picnic lately, you deserve to escape for a few blissful days. Clock off early on Friday and head to one of these weekend getaways in or near Penn Yan:

  • "Gorgeous Waterfront Home With Huge Flat Yard" is ideal for a couple of days of R&R. It comes with a range of amenities, such as a lake view and an ice maker, and is located 9 miles to the southeast of Penn Yan.
  • Or, toss a few clothes in a small suitcase and head to "Close To Wineries, Room For Families". This top-rated getaway is about 9 miles south of Penn Yan and offers a hair dryer and a water park.

Can I find studio apartments for rent in and around Penn Yan?

You sure can. If you want a simple yet stylish stay, you can't go past a studio apartment. These compact properties ooze charm and are often conveniently placed in the heart of town. Check out the following options in or near Penn Yan:

  • One of our top picks is "Quiet And Cozy Cabin With 165 Ft. Private Beach On Seneca Lake. Lgbtq+ Friendly". Book a few nights or longer at this popular stay and you'll have access to a nearby laundromat and a fridge.
  • "Lakeside Cottage On Quiet Private Road Walk To Keuka Lake State Park" is another top choice, offering all you need for a heavenly Penn Yan retreat. Useful amenities here include a free nearby fitness center and winery tours.

Can I find short term rentals in or near Penn Yan?

From affordable studio apartments to sprawling vacation homes, Vrbo has your vacation sorted. Here are two of our favorite stays in and around Penn Yan:

  • For a memorable vacation, you can't go wrong with "Grey's Getaway Cabin# 3 Finger Lakes Area". It's nice and close to the center of Penn Yan, in addition to countless things to see and do.
  • "A Beautiful, Fully Furnished Log Cabin Overlooking Keuka Lake" is also well located. Settle in here and discover why guests rate this property as one of their favorites.

What are the best romantic weekend getaways in or near Penn Yan?

Nothing says "I love you" like a romantic weekend rendezvous. If you're longing to spend a couple of nights away with your honey, we've got some romantic getaways in and around Penn Yan that will sweep you off your feet:

  • Around 7 miles from Penn Yan, "Quiet And Cozy Cabin With 165 Ft. Private Beach On Seneca Lake. Lgbtq+ Friendly" is a perfect place for doting lovebirds. Beauty services and winery tours are among the many amenities you'll find here.
  • Alternatively, spend your mini break sipping on bubbly and canoodling at "Cabin - Amazing Sunsets Overlooks A Working Vineyard", around 9 miles from Penn Yan. A fireplace and winery tours will help set the scene for romance.

What are the best large group vacation rentals in or near Penn Yan?

Share your trip and multiply the fun. Whether you're organizing an adventurous escape with your besties or a big family get-together, there's no shortage of large group vacation rentals in and near Penn Yan:

  • Offering comfort, space and privacy, you'll get your guests' stamp of approval at "Lair At The Lake" Cottage". Up to 14 people can stay at this property which has 4 bedrooms, a kitchen and a firepit. You'll find it around 1 mile to the south of Penn Yan.
  • Nothing takes priority over spending time with loved ones, and "Keuka Lake Fun And Sun" is the ideal place to do that. Located around 7 miles to the south of Penn Yan, as many as 14 guests can stay in this vacation rental which has 4 bedrooms. A garden and a kitchen are among the many amenities at hand here.

What are the best houses for rent with a pool in or near Penn Yan?

Nothing says fun and frivolity like a pool does. Blow up your inflatable doughnut and check out these houses in or near Penn Yan that feature this vacation essential:

  • Pack your swim gear and book a few days or more at "Serenity Zen House On Seneca Lake". There are also lots of other convenient amenities here, including towels and a DVD player.
  • Otherwise, enjoy a change of scenery at "Sampson House In Penn Yan". Along with an invigorating pool, you can also make use of a barbecue grill and a TV.

Penn Yan has a humid continental climate, with average summertime temperatures ranging from 55 ºF to 75 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Penn Yan vacation rental and plan your escape for whatever season you like.

What are the best large family vacation rentals in or near Penn Yan?

Whether you're escaping with the kids or you're bringing your cousins, parents and great aunt along, family vacations mean fun. These large rentals in and around Penn Yan have space for everyone — along with everything you need to keep them all happy:

  • About 9 miles to the south of Penn Yan, "Close To Wineries, Room For Family" has 4 bedrooms and can fit up to 8 guests. Some amenities here include childrens activities and towels.
  • Another top option is "Grey's Getaway Cabin# 3 Finger Lakes Area". It's around 8 miles west of Penn Yan, has 3 bedrooms and can accommodate up to 9 guests. Handy amenities here include free toiletries and a dishwasher.

If you're in the mood for visiting some family-friendly attractions nearby, Clarks Gully is a fun day out for all ages.

Can I find family cabin rentals in or near Penn Yan?

Escape the hustle and bustle and treat your loved ones to a different sort of vacation. Stay in one of these family cabins in or near Penn Yan and get the camping experience — minus the tents and with all the creature comforts!

  • "Cabin - Amazing Sunsets Overlooks A Working Vineyard" - Located around 9 miles south of the center of Penn Yan, this family-friendly getaway comes with a barbecue grill and a fridge.
  • "Grey's Getaway Cabin# 3 Finger Lakes Area" - This property is also ideal for a family getaway and is around 8 miles west of Penn Yan. Offering a porch, a living room and more, it'll get everyone's seal of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Penn Yan vacation rental that's perfect for your needs.