Winesburg Vacation Packages

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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.

Top Winesburg Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was CA $1,359, price is now CA $1,050 per person
CA $1,050
per person
Aug 27 - Sep 1
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Cleveland (CLE)
8.8/10 Excellent! (534 reviews)
Not agreeing with the 8 of 10 stars rating. The hotel isn't their focus. They are more interested in the thirsty pony business which has 2 bars, one restaurant and a lot of betting. Shower plumbing confusing. Shower handle all the way up was off turn it to the left toward the hot side and only cold water, but turn it to the right and it is hot. Way too hot at first. Air vent in bathroom filled with dust, looks like it wasn't cleaned in months. Beds were comfortable. Room was dark. They did offer an assortment of free taste test beers in the mini fridge. Probably a great place to stay if you wanted to party and bet there and then walk back to the room. They only have 9 rooms in the whole place

Reviewed on Jul 20, 2026

DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
Price was CA $1,604, price is now CA $1,337 per person
CA $1,337
per person
Sep 23 - Sep 28
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Akron (CAK)
8.6/10 Excellent! (830 reviews)

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Price was CA $2,025, price is now CA $1,695 per person
CA $1,695
per person
Sep 23 - Sep 28
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9.2/10 Wonderful! (7 reviews)

Kelleys Island Venture Resort

Kelleys Island Venture Resort

2 out of 5
Price was CA $1,957, price is now CA $1,663 per person
CA $1,663
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Cleveland (CLE)
8.6/10 Excellent! (65 reviews)
The property is a motel. The location is good. There is an outside bar/restaurant right across the parking lot that’s very nice. The rooms are dated and need updating. Our AC unit was leaking, the carpet was wet all around it. Carpets were dirty. We enjoyed the pool area, but the pool could use some maintenance also. The hot tub is not hot, but luke warm.

Reviewed on Jul 18, 2026

Quality Lodge

Quality Lodge

2.5 out of 5
Price was CA $1,382, price is now CA $1,197 per person
CA $1,197
per person
Aug 27 - Aug 31
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Cleveland (CLE)
7.8/10 Good! (348 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! (312 reviews)
"The historic Stone Cottage was wonderful. We all looked through the book regarding the renovations...wow! It is an amazing accomplishment. The location was perfect. We walked for ice cream, pizza, and coffee. Watching softball games from the screened in patio was a bonus."

Reviewed on Jun 22, 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
The price is CA $183 per night from Aug 2 to Aug 3
CA $183
CA $207 total
Aug 2 - Aug 3
includes taxes & fees
9.8/10 Exceptional! (1,372 reviews)
"Can't say anything bad about this stay, room was nice, breakfast was delicious and had several options, and staff were friendly and helpful."

Reviewed on Jul 22, 2026

Carlisle Inn Sugarcreek
Berlin Grande Hotel

Berlin Grande Hotel

2.5 out of 5
4787 Township Rd. 366 Millersburg OH
The price is CA $214 per night from Aug 12 to Aug 13
CA $214
CA $242 total
Aug 12 - Aug 13
includes taxes & fees
9.4/10 Exceptional! (1,038 reviews)
"Room was very clean, staff were pleasant loved the little balcony. Cannot comment on breakfast because we had other plans. Enjoyed our stay and will stay again."

Reviewed on Jul 22, 2026

Berlin Grande Hotel
See all 555 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.
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Frequently asked questions

How much does a Winesburg vacation package cost?
You'll find cheap prices from CA $1,050 on Expedia for your Winesburg getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Winesburg costs.
What are the cheapest months to go to Winesburg?
If you'd like to book a cheap Winesburg vacation package, consider visiting in January, February and November. You'll typically find better rates on flights and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Winesburg?
The ideal length for your Winesburg vacation depends on what you'd like to do. Usually, a handful of days to a week will give you plenty of time to tick off all the main attractions and discover some hidden treasures along the way.
How to find the best Winesburg package deals?
Begin your search for a Winesburg package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winesburg package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winesburg adventure underway.
Is it cheaper to book a Winesburg vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Winesburg vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Winesburg?
If you have your Winesburg travel dates confirmed, book as early as you can to snap up some outstanding deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Winesburg?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the available activities will also help you decide when to vacation in Winesburg.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to save for your trip to Winesburg. Then, select a property that suits your budget, whether that's an affordable option or a high-end getaway.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to experience in Winesburg. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Winesburg vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.