Penn Yan Vacations from $505

Book a Hotel + Flight or Car together to unlock savings

Photo by Shannon Willitts
    deals illustration

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, 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.
Cayuga Blu Hotel

Cayuga Blu Hotel

2 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Ithaca (ITH)
7.2/10 Good! (808 reviews)
Convenient location and filling complimentary buffet. Staff was very friendly. Outdoor pool was nice. Rooms and hotel could use an upgrade.

Reviewed on Jul 6, 2025

Inns of Aurora Resort & Spa

Inns of Aurora Resort & Spa

4.5 out of 5
Save 100% on your flight
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Ithaca (ITH)
9.8/10 Exceptional! (394 reviews)
The property was beautiful and quiet. Besides being in a beautiful location there were many activies available to do such as winery tours, paddle biarding, spa etc. If there were any questions or needs we simply sent a text and within a couple minutes we received an answer. Attention to detail was amazing as well! Even simple little things such as a light in the closet, info on how much caffeine was in the coffee pod, firepit lit at night with supplies for smores, best granola bar I've ever had. It was one of the best vacations I've had in a long time. If you want a quiet getaway I'd definitely recommend Inns of Aurora!

Reviewed on Jun 30, 2025

Gothic Eves Inn and Spa Bed and Breakfast

Gothic Eves Inn and Spa Bed and Breakfast

4 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Ithaca (ITH)
9.6/10 Exceptional! (71 reviews)
The property was nice, but I do not think it warrants such a high price. We have stayed in many BnB over the years, and this was one was a pricey ones. And we have stayed many times in the area, so we know the prices for stays. I was expecting more, a bit more pampering. Towels were scratchy, the bathrobe non absorbing because it was polyester not cotton.The light in shower didn’t work, along with a very difficult shower knob on turning water on and off. The water ran a lot longer because we couldn’t get it to turn off. I afraid we would break it. Very loud window room air conditioner. Also, altjough we did not use it, there was a charge to use the hottub. I have never encountered that. Host very nice, breakfast was great.

Reviewed on Jul 10, 2025

Benn Conger Inn

Benn Conger Inn

3.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Ithaca (ITH)
9.8/10 Exceptional! (72 reviews)
Beautiful property and great breakfast

Reviewed on Jul 11, 2025

Stratton Creek Inn

Stratton Creek Inn

2 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Ithaca (ITH)
9.8/10 Exceptional! (30 reviews)
The property was secluded but only minutes from Ithaca and all we planned to do. Bed was very comfortable and the innkeeper was so nice and accommodating. Breakfast is amazing. Couldn't ask for a nicer stay. We will be back when in the area.

Reviewed on Nov 4, 2024

Don't see what you're looking for?
See all available trips from Columbus to Penn Yan
View all trips

Discover the most popular places to visit in Penn Yan

One of the highest rated wineries in the Finger Lakes has a club and a beautiful cafe with a view of Seneca Lake

Fox Run Vineyards

4.5/5(10 reviews)

You can enjoy a tasting or tour at Fox Run Vineyards during your travels to Penn Yan. Check out the top-notch restaurants or wineries in this walkable area.

Fox Run Vineyards

The Windmill Farm & Craft Market

4.5/5(6 reviews)

You can search for that perfect souvenir at The Windmill Farm & Craft Market during your visit to Penn Yan. Amble around this relaxing area's lakeside and enjoy its top-notch restaurants.

The Windmill Farm & Craft Market

Keuka Lake Outlet Trail

5/5(2 reviews)

You can take time to visit Keuka Lake Outlet Trail during your travels to Penn Yan. Stroll along the lakeside in this relaxing area, or check out its top-notch restaurants.

Keuka Lake Outlet Trail

Penn Yan Hotel Deals

Microtel by Wyndham Penn Yan Finger Lakes Region
Microtel by Wyndham Penn Yan Finger Lakes Region
3 out of 5
124 Elm St, Penn Yan, NY
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $132 total per night from Jul 14 to Jul 15
$132 total
Jul 14 - Jul 15
Total includes taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Clean, reasonable price, efficiently run. No hiccups."

Reviewed on Jul 7, 2025

Microtel by Wyndham Penn Yan Finger Lakes Region
Hampton Inn Penn Yan
Hampton Inn Penn Yan
2.5 out of 5
110 Mace Street, Penn Yan, NY
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $146 total per night from Jul 20 to Jul 21
$146 total
Jul 20 - Jul 21
Total includes taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Pet friendly. Lake front."

Reviewed on Jul 9, 2025

Hampton Inn Penn Yan
Best Western Plus Vineyard Inn & Suites
Best Western Plus Vineyard Inn & Suites
2.5 out of 5
142 Lake St, Penn Yan, NY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Jul 20 to Jul 21
$142 total
Jul 20 - Jul 21
Total includes taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"Everyone there is so friendly and helpful."

Reviewed on Jun 30, 2025

Best Western Plus Vineyard Inn & Suites
See all 2,036 properties in Penn Yan
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

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Penn Yan vacation package cost?
You'll find cheap prices from $505 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?

  1. Pick your dates: The things you want to do in Penn Yan and your favorite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.