Greenup Vacations from $319
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Your Greenup Vacation
Food, history, entertainment and more … It's all waiting for you with a Greenup vacation package. And with the ability to customize your city adventure, you know it'll be one that's memorable. Ready to see the sights? Spend some time exploring major attractions like Jackson Truss Covered Bridge during your trip to Greenup. Your ultimate Greenup vacation is just clicks away. Search hotels, flights and more on Expedia for a getaway that's tailored to suit your style.
The Latest Greenup Vacation Packages
- Wingate by Wyndham Owensboro
Dec 12 - Dec 15Wingate by Wyndham Owensboro + Flight
Owensboro3 nights3.0 star property7.6/10 - Good (944 reviews)"Clean property overall. Good breakfast"Reviewed November 3, 2026Roundtrip • Orlando (MCO) - Evansville (EVV)MCO - SDF • Nonstop SDF - MCO • Nonstop$337$319found 20 hours agoper traveler - Residence Inn by Marriott Evansville East
Dec 12 - Dec 15Residence Inn by Marriott Evansville East + Flight
Evansville3 nights3.0 star property8.6/10 - Excellent (578 reviews)Roundtrip • Orlando (MCO) - Evansville (EVV)MCO - EVV • Nonstop EVV - MCO • 1 stop$690$599found 14 hours agoper traveler - New Harmony Inn Resort and Conference Center
Dec 12 - Dec 15New Harmony Inn Resort and Conference Center + Flight
New Harmony3 nights3.0 star property9.0/10 - Wonderful (580 reviews)"Our room had the most comfortable bed I have slept on in a long time. The room was clean and had everything needed. The only drawback to this hotel is that it is ageing, so the elevator rattles, the hallways are dark, and the room key cards are unreliable (the desk clerk warned us to keep them away from phones and other electronics, but even though we did, one stopped working). That said, the hotel is in a perfect and beautiful location, and we would stay there again."Reviewed October 25, 2026Roundtrip • Orlando (MCO) - Evansville (EVV)MCO - EVV • Nonstop EVV - MCO • 1 stop$698$631found 10 hours agoper traveler - Best Budget Inn
Dec 12 - Dec 15Best Budget Inn + Flight
Tell City3 nights2.5 star property5.2/10 - (258 reviews)"They can most definitely do better."Reviewed September 28, 2026Roundtrip • Orlando (MCO) - Evansville (EVV)MCO - SDF • Nonstop SDF - MCO • Nonstop$341$324found 20 hours agoper traveler - Rodeway Inn Mount Vernon, IN
Dec 12 - Dec 15Rodeway Inn Mount Vernon, IN + Flight
Mount Vernon3 nights2.0 star property6.0/10 - (180 reviews)Roundtrip • Orlando (MCO) - Evansville (EVV)MCO - EVV • Nonstop EVV - MCO • 1 stop$593$565found 10 hours agoper traveler
Where to stay near Greenup
Toledo
For families and nature enthusiasts looking for a memorable trip, Toledo offers a charming blend of outdoor beauty and rich history. This welcoming city is home to attractions like the historic Lincoln Log Cabin, the picturesque Jackson Truss Covered Bridge, and the serene Haughton Park, perfect for those seeking adventure or a romantic getaway. Located about 5 miles from Greenup, Toledo's unique offerings make it an ideal choice for your stay, ensuring a delightful experience for all visitors.
Jewett
Plan your stay in Jewett, a charming destination for family and nature enthusiasts eager to explore the local history and scenic beauty. Just a short distance from Greenup, Jewett offers access to highlights like the historic Jackson Truss Covered Bridge, Haughton Park for outdoor activities, and the Lincoln Log Cabin, where visitors can delve into the area's rich past. With its inviting atmosphere and diverse attractions, Jewett is an ideal choice for a memorable getaway.
Hidalgo
Make the most of your visit by staying in Hidalgo, a haven for nature lovers and adventure seekers thanks to its stunning outdoor scenery and recreational options. Explore highlights like the historic Jackson Truss Covered Bridge and enjoy family time at Haughton Park, or marvel at the World's Largest Mailbox. Located about 6 miles from Greenup, Hidalgo offers a blend of tranquility and excitement, making it a smart choice for your vacation stay.
Casey
Immerse yourself in Casey, where families and nature enthusiasts can easily access unique attractions like the World's Largest Mailbox, the World's Largest Yardstick, and the World's Largest Wind Chime. This city offers a perfect blend of outdoor adventure and scenic beauty, making it ideal for those looking to explore recreation areas and campgrounds. Located about 10 miles from Greenup, Casey is a smart choice for your next vacation, providing an unforgettable experience for all visitors.
Rose Hill
Travelers visiting the area often choose Rose Hill, especially families and nature enthusiasts seeking a tranquil getaway. With attractions like the Sam Parr State Fish and Wildlife Area for outdoor adventures, the Jasper County Museum for a glimpse into local history, and the picturesque Jackson Truss Covered Bridge, there's something for everyone. Rose Hill is conveniently located about 10 miles from Greenup, making it a smart choice for your stay in this charming region.
Greenup Hotel Deals
"Nothing wrong, great place to stay"
Days Inn & Suites by Wyndham Casey
Days Inn & Suites by Wyndham Casey
"Everything was great!"
"All staff were friendly & helpful! Our only struggle was that the carpet in our room was damp, which we discovered when our socks were wet from walking on it, and my pants were wet from sitting down on the carpet. Come to find out, all room carpets had been professionally cleaned that day! We’re thankful they were cleaned, but that would have been nice to have been forewarned!"
La Quinta Inn & Suites by Wyndham Effingham
La Quinta Inn & Suites by Wyndham Effingham"This was my second stay here and the property is always clean. stay is nice and helpful"
Fairfield Inn & Suites Marriott Effingham
Fairfield Inn & Suites Marriott Effingham
Country Inn & Suites by Radisson, Effingham, IL
Country Inn & Suites by Radisson, Effingham, IL"M"
Frequently Asked Questions
How much does a Greenup vacation package cost?
You can grab a vacation package to this popular destination from $319 on Expedia. However, how much your vacation to Greenup costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Greenup?
December, January and February are the best times to search for cheap Greenup vacation packages. Opting to travel in less busy months means you can usually find better prices on hotels and flights.
How many days is enough for Greenup?
The ideal length for your Greenup vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to hit all the main attractions and discover some hidden gems along the way.
How to find the best Greenup package deals?
Begin your search for a Greenup package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Greenup package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Greenup escape off to a flying start.
Is it cheaper to book a Greenup vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can customize your Greenup escape to match your exact style. 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 Greenup?
If you're considering a spontaneous Greenup getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Greenup vacation packages?
If you're anything like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Greenup break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.