Winesburg Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Winesburg Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
TownePlace Suites by Marriott Cleveland Solon
$636
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this business-friendly hotel in Solon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Freeway Lanes and South Chagrin Reservation are located nearby.
Excellent staff
Reviewed on Sep 7, 2026
Fidelity Hotel
Downtown Cleveland
$815
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this luxury hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Rock and Roll Hall of Fame and JACK Cleveland Casino are located nearby.
Great location within convenient walking distance to Guardians and Cavs games. Surprisingly good restaurant with a discount when you charge your meal to your room. Front desk staff and wait staff in the restaurant were very cordial and helpful. I was in Cleveland for the weekend to attend a couple of Guardians games and the competitive rate I received booking through Expedia made me pick this hotel rather than the comparable chain hotels in downtown Cleveland.
Reviewed on Sep 10, 2026
Courtyard by Marriott Cleveland University Circle
University Circle
$787
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this business-friendly hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Rock and Roll Hall of Fame and Progressive Field are located nearby.
Unsure why my room was never cleaned. I don’t understand why the restaurant/bar is closed on the weekend.
Reviewed on Aug 30, 2026
Kimpton Schofield Hotel by IHG
Downtown Cleveland
$670
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this luxury hotel in Cleveland. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rock and Roll Hall of Fame and Rocket Arena are located nearby.
Hotel Cleveland, Autograph Collection
Downtown Cleveland
$842
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this historic hotel in Cleveland. Enjoy breakfast (surcharge), a fitness center, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Rock and Roll Hall of Fame and JACK Cleveland Casino are located nearby.
InterContinental Suites Hotel Cleveland by IHG
Fairfax
$721
per person
Nov 24 - Nov 30
found 9 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Cleveland (CLE)
Book a stay at this business-friendly hotel in Cleveland. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rock and Roll Hall of Fame and Progressive Field are located nearby.
I pick this hotel based on the proximity to the Cleveland clinic. It did not disappoint me. The hotel staff was amazing, Hugh shoutout to the morning staff for answering all of my questions. As a solo traveler I felt so safe. House keeping was amazing. I am so sad I am horrible with names because they deserve a personal shoutout. Taco Tuesday is a must. Don’t forget to stop at the bar; great selection and you might encounter some great people, I did. Highly recommend staying here.
Reviewed on Sep 5, 2026
Winesburg Vacation Packages
Trying to save both time and money on your next vacation to Winesburg? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Winesburg trip one to remember. With just a few clicks, you can choose the best Winesburg vacation package for you. AARP Travel Center has a huge selection of flights and lodgings, as well as local activities to pick from.
Winesburg Hotels
With 574 hotels and resorts in Winesburg to choose from, you will find one that is perfect for you.
From Winesburg hotels with pools and on-site restaurants, to boutique accommodations that add all the extra amenities, you'll find a hotel here that will make your trip astounding. With AARP Travel Center's Winesburg hotel packages, you not only get a great rate on your flight, but also a great place to stay.
Things to do in Winesburg
Winesburg is the ideal town when you need to get away from it all. With only around 368 people in the city, this hidden-gem is good for a quite vacation.
The AARP Travel Center "Things to Do" page has more great activities that you can book.
Package Your Winesburg Vacation and Save
With so much going on in Winesburg, you'll be wanting to plan your outings, not spending time to searching for the hotel with the lowest rate. AARP Travel Center allows you to easily book everything you wish for, and save money on your vacation. You can coordinate your entire holiday, including things to do in Winesburg from just one place. The hardest packing you'll have to do is for your suitcase. Book now and save!
Top Hotel Deals
Berlin Grande Hotel
4787 Township Rd. 366 Millersburg OH
Stay at this hotel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Carlisle Inn Sugarcreek
1357 Old Route 39 Sugarcreek OH
Book a stay at this business-friendly hotel in Sugarcreek. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Berlin Resort
5330 County Road 201 Millersburg OH
Stay at this hotel in Millersburg. Enjoy free breakfast, free WiFi, and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our ...
Berlin Heritage Inn
4703 State Route 39 Millersburg OH
Book a stay at this business-friendly motel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Carlisle Inn Walnut Creek
4949 State Route 515 Millersburg OH
Stay at this hotel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Berlin Encore Hotel & Suites
4365 Ohio 39 Millersburg OH
Book a stay at this business-friendly hotel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Suites Hotel and Conference Center
4810 TR 366 Berlin OH
Stay at this hotel in Berlin. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Comfort Suites Wooster near University Campus
965 Dover Road Wooster OH
Book a stay at this business-friendly hotel in Wooster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Wallhouse Hotel, an Ascend Collection Hotel
2870 Cove Ln Millersburg OH
Book a stay at this business-friendly hotel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Lodging on the Square
4877 West Main Street Berlin OH
Stay at this motel in Berlin. Enjoy free breakfast, free WiFi, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Ramada by Wyndham Strasburg Dover
509 S Wooster Ave Strasburg OH
Book a stay at this business-friendly hotel in Strasburg. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
Quality Inn Wooster
2055 E Lincoln Way Wooster OH
Book a stay at this business-friendly hotel in Wooster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Sugarcreek Village Inn
206 SE Factory St. Sugarcreek OH
Stay at this hotel in Sugarcreek. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hotel Millersburg
35 W Jackson St Millersburg OH
Book a stay at this business-friendly hotel in Millersburg. Enjoy free WiFi, free parking, and room service. Popular attractions Sieverdes Millersburg Glass ...
Comfort Inn Millersburg
1102 Glen Dr Millersburg OH
Stay at this hotel in Millersburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Sat, Sep 12 - Fri, Sep 25
MCO
Orlando Intl.
CAK
Akron-Canton
$262
Roundtrip
found 2 days ago
Sat, Sep 12 - Fri, Sep 25
MCO
Orlando Intl.
CAK
Akron-Canton
$264
Roundtrip
found 2 days ago
Sat, Oct 17 - Tue, Oct 20
LGA
LaGuardia
CAK
Akron-Canton
$337
Roundtrip
found 5 days ago
Sat, Sep 12 - Fri, Sep 25
MCO
Orlando Intl.
CAK
Akron-Canton
$536
Roundtrip
found 2 days ago
Best points of interest in Winesburg
- College of Wooster Vacations
- Walnut Creek Amish Flea Market Vacations
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- The Amish Country Theater Vacations
- Clay's Park Resort Vacations
- Mt. Hope Event Center Vacations
- Wayne County Fairgrounds Vacations
- World's Largest Cuckoo Clock Vacations
- Yoder's Amish Home Vacations
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