Penn Yan Vacations from $396
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Your Penn Yan Vacation
When a city escape is calling your name, answer it with a Penn Yan vacation package. With all your travel needs in order before you leave, all you have to do here is focus on having a ball. If a sightseeing tour is on the agenda during your trip to Penn Yan, swing by major attractions like Keuka Lake Outlet Trail, The Windmill Farm & Craft Market and Keuka College. Whoever you're taking time off with and whatever the size of your budget, your dream Penn Yan vacation is just a few clicks away with Expedia.
The Latest Penn Yan vacation packages
Price found within the past 48 hours. Click for updated prices.
Stay near popular Penn Yan attractions
Keuka Lake Outlet Trail
9.6/10 (57 reviews)
Follow the historic Keuka Lake Outlet Trail through old mill remnants and stunning waterfalls. Hike or bike this 6.7-mile path connecting Penn Yan to Dresden while discovering the Finger Lakes' industrial past.
Photo by Shannon Willitts
Fox Run Vineyards
9.4/10 (55 reviews)
This Finger Lakes estate crafts award-winning wines using sustainable practices on Seneca Lake's western shore. Sample their diverse vintages, then enjoy locally-sourced dishes at the café with vineyard views.
The Windmill Farm & Craft Market
8.8/10 (64 reviews)
This sprawling Finger Lakes marketplace showcases over 175 shops with handcrafted treasures and local delicacies. Wander tree-lined paths between April and November to meet artisans and sample regional specialties.
Arts Center of Yates County
9.8/10 (9 reviews)
The Arts Center of Yates County showcases fine art, jewelry, and pottery from local artists. Explore diverse exhibits or join creative workshops in this cultural hub of the Keuka art community.
Torrey Ridge Winery
9.4/10 (23 reviews)
Sample the diverse wines, meads, and ciders at Torrey Ridge while taking in panoramic Seneca Lake views. Enjoy a tasting on the second-floor balconies for the most spectacular vineyard vistas.
Prejean Winery
9.8/10 (16 reviews)
This family-owned Finger Lakes winery crafts award-winning European-style wines in a picturesque setting. Savor a tasting in their garden gazebo or enjoy a bottle with a leisurely picnic on the grounds.
Oliver House Museum
9.8/10 (7 reviews)
This elegant 1852 Italianate mansion showcases Yates County history and the legacy of the "Publick Universal Friend." Explore six period rooms with original Victorian furnishings and fascinating Native American exhibits.
What to do in Penn Yan
Curated Wine Tasting Tour with Mexican Food Experience
$475
per adult
Penn Yan Hotel Deals
Microtel by Wyndham Penn Yan Finger Lakes Region
124 Elm St Penn Yan NY
Fully refundableReserve now, pay when you stay
$137 total
per night
Sep 20 - Sep 21
8.8/10 Excellent! (1,003 reviews)
"There was no breakfast items"
Reviewed on Sep 9, 2026
Hampton Inn Penn Yan
110 Mace Street Penn Yan NY
Fully refundableReserve now, pay when you stay
$146 total
per night
Sep 24 - Sep 25
9.4/10 Exceptional! (1,000 reviews)
"I asked for help because Expedia said that I was promised a lake view room. That is what I was charged for. My view was the parking lot. The hotel staff didn't help me even when I asked to talk to the manager. So, the staff at the desk said they would help, but couldn't. Now I need a refund of part ..."
Reviewed on Sep 8, 2026
Best Western Plus Vineyard Inn & Suites
142 Lake St Penn Yan NY
Fully refundableReserve now, pay when you stay
$129 total
per night
Sep 20 - Sep 21
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Penn Yan Vacation Packages
Penn Yan Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 5,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Keuka Lake State Park, Fox Run Vineyards and Hermann J. Wiemer Vineyard |
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Frequently asked questions
How much does a Penn Yan vacation package cost?
You'll find cheap prices from $396 on Expedia for your Penn Yan escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Penn Yan costs.
What are the cheapest months to go to Penn Yan?
You can typically find lower rates and better availability in October, November and December. Explore our cheap Penn Yan vacation packages and you could land some excellent off-season deals.
How many days is enough for Penn Yan?
To get the most out of a Penn Yan vacation, we suggest booking for 2 days. Split your time between visiting Keuka Lake Outlet Trail, Oliver House Museum and other leading sights, in addition to experiencing neighborhoods like Town of Milo and Town of Benton. If you've got some time to spare, add a tour or day trip to your Penn Yan vacation itinerary.
Is it worth booking a vacation package to Penn Yan?
Penn Yan has all the ingredients you need for a fantastic trip — walking trails, watersports and history are just the start. Whether you want to visit attractions such as Keuka Lake Outlet Trail and Arts Center of Yates County, or take the path less traveled, there's plenty to experience on your Penn Yan vacation.
How to find the best Penn Yan package deals?
Begin your search for a Penn Yan package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Penn Yan package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Penn Yan adventure off to a flying start.
Is it cheaper to book a Penn Yan vacation as a package?
You can enjoy significant savings on your Penn Yan retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Penn Yan?
If you're considering a spur-of-the-moment Penn Yan getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Penn Yan?
- Pick your dates: The things you want to do in Penn Yan and your favorite season will help you decide when to travel.
- Budget wisely: As well as the price of your stay, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to Penn Yan.
- Discover Penn Yan with Expedia's trip planning tool: Gain insights into the top attractions and best properties for your trip to Penn Yan. You can also save your favorite locations, collaborate with friends and family and organize all your plans in one place.
- Decide how long to go for: Now that you're up to speed on Penn Yan, you can work out the ideal length of your vacation. Create a rough plan and give yourself enough time to cover everything you want to see.
- Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the right Penn Yan vacation package for you.
- Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the best Penn Yan has to offer. Find all the fun things to do in Penn Yan with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Penn Yan vacation packages?
Secure your perfect escape to Penn Yan with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snap up cheap deals before they sell out.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
