Winesburg Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in 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 S$156 per night from 17 Aug to 18 Aug
S$156
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
"Very excellent breakfast, clean, comfortable, big rooms, counter area to eat at in rooms. We loved sitting out by the gas fire pit. Hot tub is tiny but we did get a turn. Fitness area is tiny but we were able to get in a workout."

Reviewed on 4 Aug, 2025

Berlin Grande Hotel
Carlisle Inn Sugarcreek

Carlisle Inn Sugarcreek

2.5 out of 5
1357 Old Route 39, Sugarcreek, OH
Fully refundableReserve now, pay when you stay
The price is S$143 per night from 1 Sept to 2 Sept
S$143
1 Sept - 2 Sept
includes taxes & fees
9.8/10 Exceptional! (1,171 reviews)
"This is an adorable place! Rooms are spacious and comfortable. There’s a nice balcony overlooking well tended flower beds. Rocking chairs around the fire pit. Playground kids. Complimentary cookies and popcorn in the evening. Excellent breakfast included. I love it here!"

Reviewed on 4 Aug, 2025

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
The price is S$144 per night from 10 Aug to 11 Aug
S$144
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Our stay is beautiful! I was surprised when my check in had 3 reservations when I reserved only 2 rooms and my online confirmation stated 2 rooms"

Reviewed on 4 Aug, 2025

Carlisle Inn Walnut Creek
See all 521 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.

Frequently asked questions

How much does a Winesburg holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday to Winesburg costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winesburg?
January, February and November are the best times to look for cheap Winesburg holiday packages. Travelling in less busy months means you can usually find lower prices on flights and accommodation.
How many days is enough for Winesburg?
The ideal duration of your Winesburg holiday depends on what you'd like to do. Generally, a handful of days to a week will give you time to check out all the leading sights and explore some hidden treasures along the way.
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 holiday package as early as possible.
Is it cheaper to book a Winesburg holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation 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 holiday 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.
How to plan a trip to Winesburg?

  1. Choose your travel dates: What you'd like to do in Winesburg and your preferred season can help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Winesburg. Then, choose a hotel that matches your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Winesburg. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Combine your airfare and accommodation: After you've settled on your trip dates and duration, lock in the right Winesburg holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.