Winesburg Vacations from $371

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Your Winesburg Vacation

Skip the stress of organizing your next epic adventure with a Winesburg vacation package. Whether you've come for its art, food, architecture or something else, this city offers endless possibilities for fun. Make your trip to Winesburg even more enjoyable by going sightseeing. The Amish Country Theater, Yoders Amish Home and Amish and Mennonite Heritage Center are among the top attractions worth exploring. Check out Expedia's wide range of travel options and begin planning your dream vacation to Winesburg today.

The Latest Winesburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cleveland Clinic by IHG

Holiday Inn Cleveland Clinic by IHG

3 out of 5
Fairfax
Save 100% on your flight
Price was $515, price is now $371 per person
$371
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,398 reviews)
Everything was exactly as described

Reviewed on Jun 26, 2026

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Save 100% on your flight
Price was $523, price is now $381 per person
$381
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.8/10 Excellent! (1,009 reviews)
Our room had been recently updated. It was very clean. The room had plenty of outlets for charging phones. The beds were very comfortable with an ample amount of pillows. I would highly recommend

Reviewed on Jun 21, 2026

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $570, price is now $415 per person
$415
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.4/10 Very Good! (1,740 reviews)
Great place to stay, clean comfortable room. Lots of activities to do around the area. Was a very convenient place to stay. Will definitely be back again in the future.

Reviewed on Jun 26, 2026

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Save 100% on your flight
Price was $761, price is now $563 per person
$563
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.6/10 Exceptional! (5 reviews)
Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $556, price is now $412 per person
$412
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,005 reviews)
Perfect place to stay to take in a ballgame! Highly recommend!

Reviewed on Jun 27, 2026

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Winesburg Hotel Deals

Peaceful, Spacious, Historic Stone Cottage Getaway

Peaceful, Spacious, Historic Stone Cottage Getaway

Dundee OH
10/10 Exceptional! (311 reviews)
"Perfect getaway cottage with a small town feel. We enjoyed watching the local softball games at the park located directly behind the cottage.In the mornings we would have a quick breakfast before heading out for the day. The kitchen was well stocked with cups, plates, etc. After exploring the area ..."

Reviewed on Jun 8, 2026

Get rates
Peaceful, Spacious, Historic Stone Cottage Getaway
Carlisle Inn Sugarcreek

Carlisle Inn Sugarcreek

2.5 out of 5
1357 Old Route 39 Sugarcreek OH
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $147 total per night from Jun 30 to Jul 1
$147 total
Jun 30 - Jul 1
Total with taxes and fees
9.8/10 Exceptional! (1,377 reviews)
"Noteworthy: check in early and Be sure to book directly with the hotel, not a 3rd party booking site even though for 2 rooms, it was $400 cheaper. I hope our experience was a one-off. We were confronted upon check-in with little slips of paper and numbers to call to deal with a glitch caused by the ..."

Reviewed on Jun 26, 2026

Carlisle Inn Sugarcreek
Berlin Grande Hotel

Berlin Grande Hotel

2.5 out of 5
4787 Township Rd. 366 Millersburg OH
$109 nightly
The price is $124 total per night from Jul 5 to Jul 6
$124 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (1,013 reviews)
"Clean room! Nice breakfast! Wished we had another night or two booked to enjoy the amenities!"

Reviewed on Jun 27, 2026

Berlin Grande Hotel
See all 551 properties in Winesburg
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 Winesburg Vacation Packages

Winesburg Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Akron-Canton Airport (CAK)
Population
350
Top Sights
Ohio Star Theater at Dutch Valley, The Amish Country Theater and Breitenbach Wine Cellars

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Frequently asked questions

How much does a Winesburg vacation package cost?
Offering excellent value package deals from $371 on Expedia, you'll be surprised at how little a vacation to Winesburg costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winesburg?
You can generally find lower prices and better availability in November, December and January. Check out our cheap Winesburg vacation packages and you could land some great off-season discounts.
How many days is enough for Winesburg?
With a well-planned schedule, you can easily tick off the top Winesburg sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Winesburg vacation for longer.
How to find the best Winesburg package deals?
Use Expedia's filter tool to find some great Winesburg package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Winesburg package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Winesburg vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and accommodations separately. Better still, you can tailor your Winesburg getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winesburg?
If you're considering a spur-of-the-moment Winesburg adventure, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winesburg vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Winesburg trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.