A covered bridge with 'JACKSON, N.H.' sign, speed limit 15, and 'NO PARKING ANY TIME' sign.

Greenup Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Greenup vacation rentals

A wooden cabin entrance with a welcome sign, a small table with a lamp and flowers, and a woven mat on the floor.

1. Vintage Charmer on Main Street

Vintage Charmer on Main Street
Greenup
10.0 out of 10, Exceptional, (79 reviews)
"Great stay !"
United States
chris H.
$133 nightly
The price is $141
Oct 24 - Oct 25
Total with taxes and fees
Vintage Charmer on Main Street
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

2. Cottage By The Park Home of The Big Things

Cottage By The Park Home of The Big Things
Casey
10.0 out of 10, Exceptional, (69 reviews)
"The house is lovely and super clean. The beds were comfortable and there's lots of room to move in the bathrooms. The house is located across the street from the park, which was lovely for morning and evening walks. Casey is a cute town to visit. We enjoyed our stay!"
United States
Meg B.
$237 nightly
The price is $251
Oct 27 - Oct 28
Total with taxes and fees
Cottage By The Park Home of The Big Things
A cozy living room with a sofa, a small side table, and a dining area with a table and chairs. A kitchen is visible in the background.

3. Park View Place 4 Blocks From the World's Biggest

Park View Place 4 Blocks From the World's Biggest
Casey
9.8 out of 10, Exceptional, (45 reviews)
"Cozy and clean. Enjoyed our stay. Kids loved that the park was so close!"
United States
Angie R.
$216 nightly
The price is $238
Oct 26 - Oct 27
Total with taxes and fees
Park View Place 4 Blocks From the World's Biggest
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

4. Family Friendly Cottage in the Countryside

Family Friendly Cottage in the Countryside
Toledo
10.0 out of 10, Exceptional, (3 reviews)
"Super clean and quiet was a great place to get away while visiting family and friends."
United States
Richard
$420 nightly
The price is $424
Oct 24 - Oct 25
Total with taxes and fees
Family Friendly Cottage in the Countryside
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

5. Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL

Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
Martinsville
10.0 out of 10, Exceptional, (10 reviews)
"Simple easy quite in the woods brand new clean nice fire pit perfect for a short stay would be awesome to rent for hunting season"
United States
J M.
$215 nightly
The price is $228
Oct 28 - Oct 29
Total with taxes and fees
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

6. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (15 reviews)
"Very cool space in a great location "
United States
Stewart T.
$186 nightly
The price is $197
Nov 2 - Nov 3
Total with taxes and fees
Cozy 2BR Loft in Downtown Charleston, IL
A tent set up on a wooden platform surrounded by trees.

7. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
$74 nightly
The price is $78
Oct 26 - Oct 27
Total with taxes and fees
Bell Tent Under the Stars
A brick house with a white door, a mailbox, and a wooden porch.

8. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (53 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
$170 nightly
The price is $180
Oct 26 - Oct 27
Total with taxes and fees
Brickway Retreat
A modern kitchen with a brick wall, a bar area with stools, and a large island.

9. The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed

The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
Effingham
10.0 out of 10, Exceptional, (14 reviews)
"Loved the atmosphere very unique and comfortable. Would highly recommend and will definitely stay the next time we travel this way"
United States
Roger
$198 nightly
The price is $212
Oct 25 - Oct 26
Total with taxes and fees
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
An open-plan office with exposed brick walls, wooden floors, and large windows.

10. The Exchange. Cozy Studio., XCHNG Studio

The Exchange. Cozy Studio., XCHNG Studio
Effingham
10.0 out of 10, Exceptional, (36 reviews)
"Wonderful place, love the location. "
United States
Dawn K.
$167 nightly
The price is $179
Nov 1 - Nov 2
Total with taxes and fees
The Exchange. Cozy Studio., XCHNG Studio
A bar area with a wooden ceiling and bar stools.

11. The Exchange. Loft Living.

The Exchange. Loft Living.
Effingham
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful stay! Second time we've stayed with them & it's great! "
United Kingdom
Erica C.
$216 nightly
The price is $232
Nov 18 - Nov 19
Total with taxes and fees
The Exchange. Loft Living.
A spacious kitchen with a large island, exposed brick walls, and large windows offering views of the city.

12. The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.

The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
Effingham
10.0 out of 10, Exceptional, (28 reviews)
"Amazing location and the property was perfect! Great communication with our host."
United States
Lynn M.
$296 nightly
The price is $316
Oct 25 - Oct 26
Total with taxes and fees
The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
A hotel with a covered entrance, multiple balconies, and a parking lot.

13. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"Lobby had clear signs and felt straightforward on arrival."
United States
Anonymous traveler
$59 nightly
The price is $66
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
A hotel room with a bed, a nightstand, a lamp, and a window with curtains.

14. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"There was ample room for our group to spread out with easy parking nearby. Location felt perfect for visiting local attractions."
United States
Anonymous traveler
$63 nightly
The price is $71
Oct 26 - Oct 27
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A hotel room with a bed, two bedside lamps, a nightstand, and a wooden floor.

15. 1 King Bed | Smoking, Micfridge

1 King Bed | Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed the double king bed, ideal for two. Plenty of space and comfortable enough for a good rest."
United States
Anonymous traveler
$77 nightly
The price is $86
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Smoking, Micfridge
A hotel reception area with a counter, a digital tablet, and a poster on the wall.

16. 3 Queen Beds | Non-Smoking, Kitchen

3 Queen Beds | Non-Smoking, Kitchen
Effingham
10.0 out of 10, Exceptional, (4 reviews)
$96 nightly
The price is $108
Oct 25 - Oct 26
Total with taxes and fees
3 Queen Beds | Non-Smoking, Kitchen
A reception area with a large number '6' on the wall, a counter, and a digital display.

17. 1 Queen Bed | Non-Smoking, Micfridge

1 Queen Bed | Non-Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (5 reviews)
$52 nightly
The price is $58
Oct 26 - Oct 27
Total with taxes and fees
1 Queen Bed | Non-Smoking, Micfridge
A spacious kitchen with a long counter, a dining area with chairs, and large windows providing natural light.

18. 1 Queen Bed | Smoking, Micfridge

1 Queen Bed | Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (4 reviews)
"A calm spot ideal for a quick stopover."
United States
Anonymous traveler
$69 nightly
The price is $78
Oct 26 - Oct 27
Total with taxes and fees
1 Queen Bed | Smoking, Micfridge
Three beverage vending machines with various drink options.

19. 2 Queen Beds | Smoking, Micfridge

2 Queen Beds | Smoking, Micfridge
Effingham
10.0 out of 10, Exceptional, (5 reviews)
$81 nightly
The price is $91
Oct 26 - Oct 27
Total with taxes and fees
2 Queen Beds | Smoking, Micfridge
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 Effingham by IHG

Holiday Inn Effingham by IHG

10/10 Excellent
"Clean"
Vickie 1-night trip
Posted 23 hours ago
Holiday Inn Effingham 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 $141 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.

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 Wooden Shoes.

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.