Winesburg Vacations

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Find the Best Winesburg Vacation Packages

Winesburg Hotel Deals

Peaceful, Spacious, Historic Stone Cottage Getaway
Peaceful, Spacious, Historic Stone Cottage Getaway
Dundee
9.8/10 Exceptional! (274 reviews)
Loved Stone Cottage Inn
"The Stone Cottage is absolutely charming. My son and daughter in law both had to work one day, so the basement worked out beautifully. The loft and rooms were all cozy and comfortable. Kitchen was equipped abundantly. The location next to Beacon Cafe was amazing, food was so good. Whitmers General ..."

Reviewed on 3 March 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
10/10 Exceptional! (87 reviews)
Blessings was a blessing!!!
"What a wonderful time with friends in the Blessing House! Beautifully decorated, lots of amenities supplied! Wonderful to meet the owners while visiting their horses in the stable! Will be back!!!"

Reviewed on 30 March 2025

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Farmhouse of Blessings | 2 Bed, 2 Bath
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 AED 345 per night from Apr 20 to Apr 21
AED 345
AED 390 total
includes taxes & fees
20 Apr - 21 Apr
9.6/10 Exceptional! (986 reviews)
"We loved looking at the frame quilts, crossstitch and lace and enjoyed reading about them."

Reviewed on 16 April 2025

Carlisle Inn Walnut Creek
See all 510 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 vacation package cost?
Offering excellent value package deals 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?
January, February and November are the best times to look for cheap Winesburg vacation packages. Traveling in less busy months means you can usually find lower prices on flights and accommodations.
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.
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 accommodations: After you’ve settled on your trip dates and duration, lock in the right Winesburg vacation package for you.