Winesburg Holidays from £958

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Your Winesburg Holiday

Skip the stress of organising your next epic adventure with a Winesburg holiday 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 Theatre, Yoders Amish Home and Amish and Mennonite Heritage Centre are among the top attractions worth exploring. Check out Expedia's wide range of travel options and begin planning your dream holiday to Winesburg today.

Top Winesburg Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Willoughby House

The Willoughby House

3 out of 5
Price was £1,288, price is now £958 per person
£958
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Cleveland (CLE)
10/10 Exceptional! (2 reviews)
Beautiful property. Nice location. Excellent lounge & restaurant.

Reviewed on 4 Aug 2025

Fidelity Hotel

Fidelity Hotel

4 out of 5
Downtown Cleveland
Price was £1,570, price is now £1,091 per person
£1,091
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Cleveland (CLE)
9.6/10 Exceptional! (291 reviews)
Cute and classy boutique hotel within walking distance to everything.

Reviewed on 17 Aug 2025

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was £1,700, price is now £1,286 per person
£1,286
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Cleveland (CLE)
8.6/10 Excellent! (1,491 reviews)
Issue w shower water temp adjustment

Reviewed on 18 Aug 2025

Kimpton Schofield Hotel by IHG

Kimpton Schofield Hotel by IHG

4.5 out of 5
Downtown Cleveland
Price was £1,386, price is now £1,059 per person
£1,059
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Cleveland (CLE)
8.6/10 Excellent! (1,012 reviews)
Super friendly staff.

Reviewed on 18 Aug 2025

InterContinental Suites Hotel Cleveland by IHG

InterContinental Suites Hotel Cleveland by IHG

4 out of 5
Fairfax
Price was £1,316, price is now £1,016 per person
£1,016
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Cleveland (CLE)
8.8/10 Excellent! (1,003 reviews)
The check in staff were super! Valet was mixed - they charge $25 a day. Out breakfast experience was poor. We arrived w

Reviewed on 18 Aug 2025

Winesburg Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Akron-Canton Airport (CAK)
Population
350
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Ohio Star Theatre at Dutch Valley, The Amish Country Theatre and Breitenbach Wine Cellars

Top hotels in Winesburg

Peaceful, Spacious, Historic Stone Cottage Getaway

Peaceful, Spacious, Historic Stone Cottage Getaway

Dundee, OH
9.8/10 Exceptional! (285 reviews)
Worth staying here
"The cottage is clean, well decorated and nicely appointed. It had everything we needed. There is a section of the yard that is fenced which worked well for our dogs. It is a unique experience to see the old stonework and the progression of the restoration in the photo album. This place has been well ..."

Reviewed on 14 Jul 2025

Get rates
Peaceful, Spacious, Historic Stone Cottage Getaway
Historic 200 year old 3-bedroom log house with WiFi and AC in charming Winesburg

Historic 200 year old 3-bedroom log house with WiFi and AC in charming Winesburg

Winesburg, OH
9.6/10 Exceptional! (12 reviews)
Winesburg cabin stay
"We loved our stay. The house was beautiful. The neighborhood so quaint. We frequented the pizza and ice cream shop right across the street and the coffee shop a couple blocks down. I did read this in other reviews so I was prepared for it and did not count it as a negative…but the house is old and ..."

Reviewed on 23 Jul 2025

Get rates
Historic 200 year old 3-bedroom log house with WiFi and AC in charming Winesburg
Berlin Grande Hotel

Berlin Grande Hotel

2.5 out of 5
4787 Township Rd. 366, Millersburg, OH
Fully refundableReserve now, pay when you stay
The price is £85 per night from 24 Aug to 25 Aug
£85
24 Aug - 25 Aug
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Toatally enjoyed our 2 night stay at the Grand - the facilty is immaculate inside and out, the room was spacious, well maintained and up to date. The breakfast was generous, hot with a great variety. The staff were all friendly and helpful. We would absolutely visit the Grand again any time."

Reviewed on 16 Aug 2025

Berlin Grande Hotel
See all 520 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

Why should I book my Winesburg holiday with Expedia?
Choose Expedia to plan your next adventure easily and all in the same place. Our insider tip for bagging an unbeatable deal on a Winesburg retreat? Bundle your airfares, hotel and/or hire car into a package holiday. Then throw in some exciting tours and activities. Most bookings also have flexible cancellation policies, so there's no need to stress if you have to switch up your travel plans. Round-the-clock help with making changes to your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Winesburg?
May, June and July are the busiest months in Winesburg, while November, December and January are generally quieter. With average daytime temperatures of -2ºC, January is the coolest month in Winesburg. The warmest month is July, when you can experience averages of 22ºC during the day. Whatever the weather conditions, you'll find a whole lot to keep you entertained here.
What is the top hotel for my holiday in Winesburg?
Offering many of the creature comforts of home, Hampton Inn Mansfield/Ontario will make the perfect base for your Winesburg escape.
How do I get a cheap holiday to Winesburg?
Combine your flights and hotels, throw in extras such as activities or a hire car, and save with a Winesburg holiday. You won't just enjoy big discounts on your escape — you'll have plenty of choice within your reach too. When you book through Expedia, you can select from more than 400 air carriers and 321,000 hotels around the world. Your next epic adventure starts right here, right now! Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Winesburg holiday?
With major attractions such as Walnut Creek Amish Flea Market and The Amish Country Theatre, a holiday in Winesburg is full of exciting places to visit. Ohio Star Theatre at Dutch Valley and The Farm at Walnut Creek are a couple of other sights also worth a look.
Do I need a visa for my Winesburg holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and the purpose of your visit, whether it be for work or holidays, will determine if you need a visa for Winesburg. Also make sure your passport is up to date and has at least six months validity remaining after your return date. Do all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Winesburg holiday?
Although everyone's fashion style varies, it can help to have some guidelines for what type of clothes to bring during your holiday in Winesburg. Consider looking up social media before you go for inspiration on local dress codes or fashion trends. Daytime temperatures during January, Winesburg's coolest month, average -2ºC. July marks this destination's warmest month when the average daily temperature reaches 22ºC. Our top tip? Take the guesswork out of what to pack and check the local weather forecast.
What does an Expedia Winesburg holiday include?
Flights, hire cars and hotels — we've got them covered. With Expedia, you can shape your Winesburg travel package however you want. All you have to do is determine what you need. Once you've made your booking, why not add extras like activities and experiences? The more you bundle, the bigger the savings! Expedia features all sorts of properties, with the most popular in Winesburg being private holiday homes and bed & breakfasts. With Expedia, you'll always have the freedom and flexibility to tailor your holiday your way.
Does Expedia offer Book Now, Pay Later Winesburg holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book an incredible getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna can help. Paying in multiple instalments will make that dream holiday possible.
  • No-deposit holidays: Hitting the "book now" button is easier with this plan. With no upfront fee for your getaway, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Winesburg Expedia holiday?
With a holiday package, you're in control. Whether you want to fly to Winesburg in coach or first class, simply select from the available airline options. Expedia has access to more than 400 partner airlines worldwide.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.