Penn Yan Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Penn Yan Vacation Packages
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
￥19,310
￥21,629 total
Aug 12 - Aug 13
includes taxes & fees
Best Western Plus Vineyard Inn & Suites
142 Lake St Penn Yan NY
Fully refundableReserve now, pay when you stay
￥17,298
￥19,374 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"The hotel has definitely been updated and was very clean!"
Reviewed on Aug 9, 2026
Hampton Inn Penn Yan
110 Mace Street Penn Yan NY
￥16,688
￥18,689 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Waterfront rooms with Keuka Lake views!"
Reviewed on Aug 7, 2026
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.
Stay near popular Penn Yan attractions
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.
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.
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.
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.
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.
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.
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.
What to do in Penn Yan
Frequently asked questions
How much does a Penn Yan vacation package cost?
You'll find cheap prices 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?
To pick up cheap Penn Yan vacation packages, organize your trip outside of peak times like public holidays and major events. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Penn Yan?
To fully enjoy a Penn Yan vacation, we recommend booking for 2 days. Divide your time between discovering The Windmill Farm & Craft Market, Keuka Lake Outlet Trail and other top attractions, as well as experiencing neighborhoods like Town of Milo and Town of Benton. If you've got some time to spare, add a day trip to your Penn Yan vacation itinerary.
Is it worth booking a vacation package to Penn Yan?
Popular for its walking trails, fishing and watersports, a Penn Yan vacation is a hit with all kinds of travelers. Be sure to visit key sights like Keuka Lake Outlet Trail and Arts Center of Yates County, and consider renting a car for day trips to explore even more.
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?
- Choose when to get away: Check your schedule and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Penn Yan.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and food to flights and activities. Your hotel will probably be the largest expense during your trip to Penn Yan.
- Decide your trip length: Consider how much time you'd like to spend discovering Penn Yan. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Penn Yan vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
