Penn Yan Vacations from $605
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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.
Geneva On The Lake
$1,094
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Ithaca (ITH)
8.8/10 Excellent! (328 reviews)
The building itself is stunning, and the staff were friendly and helpful, but unfortunately the property is not being maintained to the standard you would expect for a romantic getaway.
The front landscaping was dead and unkempt, and our room felt very dated, with stained carpets and old furniture. We also noticed cobwebs throughout the interior of the property, which really took away from the overall experience. Food was also mediocre.
It’s a shame because this hotel has so much potential. With a significant renovation and better upkeep, it could easily be a 5-star resort. Sadly, it is not there today.
We would not return under the current conditions.
Reviewed on Aug 16, 2026
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.
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
$105 nightly
$117 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Breakfast"
Reviewed on Aug 18, 2026
Best Western Plus Vineyard Inn & Suites
142 Lake St Penn Yan NY
Fully refundableReserve now, pay when you stay
$110 nightly
$123 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
"Indoor pool and hot tub clean room"
Reviewed on Aug 15, 2026
Hampton Inn Penn Yan
110 Mace Street Penn Yan NY
Fully refundableReserve now, pay when you stay
$98 nightly
$110 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
"Beautiful lake view. Nicely manicured property. Good breakfast. Comfortable beds. Nice bathroom."
Reviewed on Aug 18, 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.
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 |
More vacations you might like
Frequently asked questions
How much does a Penn Yan vacation package cost?
You'll find cheap prices from $605 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
- Rv Parks in Yates County
- Cabin Rentals in New York
- Hotels on the Lake in Penn Yan
- Historic Hotels in Penn Yan
- Hotels with an Indoor Pool in Penn Yan
- Family Hotels in Penn Yan
- Cabin Rentals in Watkins Glen
- Penn Yan Hotels
- Motels in Penn Yan
- Cheap Hotels in Penn Yan
- Rv Parks in Finger Lakes Region
- Canandaigua Hotels
- Cabin Rentals in Penn Yan
- Cabin Rentals in Keuka Park
- Luxury Hotels in Penn Yan
- Hotels with Balconies in Penn Yan
- Watkins Glen Hotels
- 5 Star Hotels in Penn Yan
- Romantic Hotels in Finger Lakes Region
- Syracuse Hotels
- Hotels with an Outdoor Pool in Penn Yan
- B&B in Finger Lakes Region
- Cabin Rentals in Yates County
- B&B in Yates County
- Hotels with Tennis Courts in Penn Yan
- Ithaca Hotels
- Hotels with Hot Tubs in Penn Yan
- 4 Star Hotels in Penn Yan
- Extended Stay Hotels in Penn Yan
- Winery Hotels in Penn Yan
- Romantic Hotels in Penn Yan
- Geneva Hotels
- Adults Only Resorts & in Finger Lakes Region
- B&B in Penn Yan
- Winery Hotels in Finger Lakes Region
- Wyndham Hotels in Penn Yan
- Inns in Penn Yan
- Hotels with smoking rooms in Penn Yan
- Resorts & Hotels with Spas in Penn Yan
- Hotels with a Pool in Penn Yan
- Pet-Friendly Hotels in Penn Yan
- Rochester Hotels
- Hotels near Watkins Glen State Park
- Cabin Rentals in Finger Lakes Region
- Apartments in Penn Yan
- Roy's Marina
- Prattsburgh Vacations
- Watkins Glen State Park
- Three Brothers Wineries and Estates
- Keuka College
- Thirsty Owl Wine Company
- King's Garden Vineyards Winery and Tasting Room
- New York Vacations
- Grist Iron Brewing Company
- Hazlitt 1852 Vineyards
- Billsboro Winery
- Middlesex Vacations
- Majestic Hills Golf Course
- Hermann J. Wiemer Vineyard
- Keuka Lake
- Glenora Wine Cellars
- Fox Run Vineyards
- Sampson State Park
- Wagner Vineyards
- Torrey Ridge Winery
- Oliver House Museum
- Keuka Lake Outlet Trail
- Mcgregor Vineyard
- The Windmill Farm & Craft Market
- Lacey Magruder Winery
- Visit Finger Lakes Region
- Hobart and William Smith Colleges
- Visit Seneca Falls
- Wells College
- Hector Vacations
- Keuka Lake State Park
- Visit Penn Yan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
