Greenup Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Greenup vacation rentals

Interior
Vintage Charmer on Main Street

Vacation Home in Greenup

Vintage Charmer on Main Street
10.0 out of 10, Exceptional, (60)
"Looking forward to staying again on our return trip home"
United States
Karen B.
$131 nightly
The price is $138
Dec 27 - Dec 28
Total with taxes and fees
Vintage Charmer on Main Street
House (3 Bedrooms) | Interior
Pet-friendly Home w/ Fenced Yard: 'cozy in Casey'

Cottage in Casey

Pet-friendly Home w/ Fenced Yard: 'cozy in Casey'
3.0 star property
10.0 out of 10, Exceptional, (1)
"Property was very clean and quiet, will definitely schedule for next family reunion."
United States
Anthony
$250 nightly
The price is $275
Jan 3 - Jan 4, 2026
Total with taxes and fees
Pet-friendly Home w/ Fenced Yard: 'cozy in Casey'
Fridge, microwave, oven, stovetop
Brickway Retreat

Vacation Home in Mattoon

Brickway Retreat
9.8 out of 10, Exceptional, (41)
"This house was perfect! Very clean, beautifully decorated and very cozy. So many nice extras. Because of bad weather we had to modify our stay and we were very grateful that the hosts were able to accommodate us. We would absolutely stay here again. "
United States
Shari
$170 nightly
The price is $180
Dec 31 - Jan 1, 2026
Total with taxes and fees
Brickway Retreat
Fridge, microwave, oven, stovetop
Cozy 2BR Loft in Downtown Charleston, IL

Apartment in Charleston

Cozy 2BR Loft in Downtown Charleston, IL
10.0 out of 10, Exceptional, (8)
"Great spot, comfortable, clean "
United States
Amanda P.
$186 nightly
The price is $197
Dec 31 - Jan 1, 2026
Total with taxes and fees
Cozy 2BR Loft in Downtown Charleston, IL
Fridge, microwave, oven, stovetop
Cottage By The Park Home of The Big Things

Cottage in Casey

Cottage By The Park Home of The Big Things
10.0 out of 10, Exceptional, (59)
"Great house, very clean, host was very responsive and friendly! Would definitely recommend staying here! "
United States
Shawna L.
$226 nightly
The price is $240
Dec 29 - Dec 30
Total with taxes and fees
Cottage By The Park Home of The Big Things
Property grounds
THE GARDEN HOUSE A FEW BLOCKS FROM THE WORLD'S LARGEST & FAIRVIEW PARK

Vacation Home in Casey

THE GARDEN HOUSE A FEW BLOCKS FROM THE WORLD'S LARGEST & FAIRVIEW PARK
9.8 out of 10, Exceptional, (40)
"Great property for a stay in Casey. Communication was great, property was great and renting the golf cart was so much fun!!"
United States
Debra B.
$260 nightly
The price is $276
Dec 29 - Dec 30
Total with taxes and fees
THE GARDEN HOUSE A FEW BLOCKS FROM THE WORLD'S LARGEST & FAIRVIEW PARK
TV, fireplace
XCHNG Corner Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.

Apartment in Effingham

XCHNG Corner Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
10.0 out of 10, Exceptional, (16)
"We stayed here to attend a conference in Effingham, great location and the owners were very responsive and easy to work with."
United States
Cole F.
$266 nightly
The price is $284
Jan 11 - Jan 12, 2026
Total with taxes and fees
XCHNG Corner Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
Smart TV
Park View Place 4 Blocks From the World's Biggest

Vacation Home in Casey

Park View Place 4 Blocks From the World's Biggest
10.0 out of 10, Exceptional, (39)
"Nice location,friendly host,and availability of a golf cart to get around town."
United States
Barbara h.
$203 nightly
The price is $215
Dec 30 - Dec 31
Total with taxes and fees
Park View Place 4 Blocks From the World's Biggest
Dining
XCHNG Downtown Loft Living

Apartment in Effingham

XCHNG Downtown Loft Living
2.0 star property
10.0 out of 10, Exceptional, (3)
"Very convenient location, Very cosy and stylish apartment, with a big variety of things to do (f.e. games, the arcade machines were great!). But also nice shops and restaurants in walking distance to explore, very quiet at night."
Germany
slatomir w.
$201 nightly
The price is $216
Jan 4 - Jan 5, 2026
Total with taxes and fees
XCHNG Downtown Loft Living
Dining
XCHNG King Bed Luxury Downtown, XCHNG. Industrial Executive Loft w/ King Bed

Apartment in Effingham

XCHNG King Bed Luxury Downtown, XCHNG. Industrial Executive Loft w/ King Bed
10.0 out of 10, Exceptional, (10)
"Our family loved staying at the Exchange. Our loft was very clean with fun decor. The location is fantastic in downtown Effingham. We enjoyed evening drinks at the Wheat Penny downstairs. We will definitely be repeat visitors!"
United States
Allison S.
$193 nightly
The price is $206
Jan 25 - Jan 26, 2026
Total with taxes and fees
XCHNG King Bed Luxury Downtown, XCHNG. Industrial Executive Loft w/ King Bed
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.
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Top Greenup Hotel Reviews

Holiday Inn Express & Suites Mattoon by IHG

Holiday Inn Express & Suites Mattoon by IHG

10/10 Excellent
"We just checked into our room but pleased with it"
Penny 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Mattoon by IHG

Find out more about Greenup

Everything you need to know about Greenup vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenup vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenup vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenup vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenup. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Greenup in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $138 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenup rentals

At Expedia, we put the best Greenup vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Greenup rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenup vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenup. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Greenup?

Yes, we give you a choice of vacation rentals close to popular attractions in Greenup, or you can go with a more remote option if you'd like a relaxing place to stay. Greenup is known for its coffeehouses and parks. Make sure you have time to check out the restaurants while you're in the area.

What are some of the best vacation home rentals that Greenup has to offer?

Vintage Charmer on Main Street: This highly rated vacation home rental in Greenup offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Greenup?

While you're exploring the area, Haughton Park and Sam Parr State Fish and Wildlife Area are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Lincoln Log Cabin and World's Largest Bird Cage.

What are vacation rentals like in Greenup?

Vacation rentals are privately owned accommodations you can book for several days or more in Greenup. Vacation rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for small groups.