Winesburg Vacations from $298

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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.
Hampton Inn & Suites Cleveland-Beachwood

Hampton Inn & Suites Cleveland-Beachwood

2.5 out of 5
Price was $381, price is now $298 per person
$298
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
9.2/10 Wonderful! (1,004 reviews)
My favorite hotel in the Cleveland area. Everything about it is 10/10. The staff have outstanding customer service. They are so friendly and welcoming. The pool and hot tub area is very clean and relaxing. Gym is very nice. Laundry facility is extremely useful, I appreciate that it accepts Apple Pay. Good breakfast. Best of all, they have clean, spacious, comfortable rooms. I joke with people and say I wish I could live there, LOL. Really it’s the best - you won’t regret staying here!

Reviewed on Apr 1, 2026

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $599, price is now $409 per person
$409
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
7.6/10 Good! (1,007 reviews)
The location was perfect, only 8min walk from the Arena and Stadium

Reviewed on May 3, 2026

The Aurora Inn

The Aurora Inn

3 out of 5
Price was $987, price is now $762 per person
$762
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Akron (CAK)
9/10 Wonderful! (633 reviews)
Unique property in a neighborhood setting. Lunch & dinner served on property in the tavern. Large indoor pool connected to the property keeps activity noise separated from accommodations area. Staff was helpful & friendly.

Reviewed on May 4, 2026

Hampton Inn Cleveland-Westlake

Hampton Inn Cleveland-Westlake

2.5 out of 5
Price was $392, price is now $306 per person
$306
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
8.2/10 Very Good! (1,004 reviews)
It was a good experience. The rooms were a bit small and the breakfast was very busy, but the staff was super friendly and helpful.

Reviewed on May 4, 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 $519, price is now $408 per person
$408
per person
Jun 12 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Cleveland (CLE)
10/10 Exceptional! (3 reviews)
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Winesburg Hotel Deals

Peaceful, Spacious, Historic Stone Cottage Getaway

Peaceful, Spacious, Historic Stone Cottage Getaway

Dundee OH
10/10 Exceptional! (305 reviews)
This was our third stay at the cottage since 2022 and, sad to say, it is lacking attention. I would suggest that the bathroom towels need to be replaced, the toilet in the main floor hallway kept stopping up and needs further attention, the double reclining chair in the living room is broken, the ...

Reviewed on Apr 21, 2026

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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
$129 nightly
The price is $145 total per night from May 17 to May 18
$145 total
May 17 - May 18
Total with taxes and fees
9.8/10 Exceptional! (1,391 reviews)
The hotel is very pretty and clean. The location is great for enjoying the Ohio Star Theater, Sugar Creek, Walnut Creek and Berlin. The front desk staff was very friendly and helpful. There is a lovely sitting area on the second floor, as well as hot drinks, water and snacks, as well as a very nice ...

Reviewed on May 4, 2026

Carlisle Inn Sugarcreek
Carlisle Inn Walnut Creek

Carlisle Inn Walnut Creek

3 out of 5
4949 State Route 515 Millersburg OH
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $124 total per night from May 10 to May 11
$124 total
May 10 - May 11
Total with taxes and fees
9.8/10 Exceptional! (1,006 reviews)
The breakfast was amazing. The only thing I would add are potatoes with the eggs and sausage. The staff is really friendly and professional

Reviewed on May 4, 2026

Carlisle Inn Walnut Creek
See all 547 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 $298 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.