Winesburg Holidays

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Winesburg Holiday

Our pick of the best Winesburg Hotel Deals

Peaceful, Spacious, Historic Stone Cottage Getaway
Peaceful, Spacious, Historic Stone Cottage Getaway
Dundee
9.8/10 Exceptional! (280 reviews)
Charming cottage
"If you are making a trip to Holmes County and surrounding areas…this charming cottage is awesome. The location is great. This cottage was built in the 1800’s and the remodeling that had been done is incredible (be sure to check out the book with the before pictures). The kitchen is well stocked with ..."

Reviewed on 25 Jun. 2025

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Peaceful, Spacious, Historic Stone Cottage Getaway
Farmhouse of Blessings | 2 Bed, 2 Bath
Farmhouse of Blessings | 2 Bed, 2 Bath
Dundee
9.8/10 Exceptional! (94 reviews)
A wonderful getaway
"My daughter and I really enjoyed our stay at this charming and welcoming farmhouse. It’s within easy distance of all attractions in this beautiful part of Amish country. We had the most lovely visits with the horses and the cats on the grounds, and we also met the property owner who could not have ..."

Reviewed on 13 Jun. 2025

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Farmhouse of Blessings | 2 Bed, 2 Bath
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 NZ$176 per night from 20 July to 21 July
NZ$176
20 July - 21 July
includes taxes & fees
9.8/10 Exceptional! (1,125 reviews)
Nice get away
"Room was amazing, peaceful and private. The negatives are: TV didn’t connect to cable, pillows were poor in quality and uncomfortable, the bed sheet was a rough fabric and the breakfast foods are better at a Comfort Inn."

Reviewed on 10 Jul. 2025

Carlisle Inn Sugarcreek
See all 526 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.