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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (75 reviews)
"Great stay !"
United States
chris H.
The price is CA $122
CA $195 total
includes taxes & fees
Sep 7 - Sep 8
Vintage Charmer on Main Street
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

2. Family Friendly Cottage in the Countryside

Family Friendly Cottage in the Countryside
Toledo
10.0 out of 10, Exceptional, (2 reviews)
"Very nice very quiet peaceful surroundings"
United States
Tony P.
The price is CA $353
CA $577 total
includes taxes & fees
Sep 7 - Sep 8
Family Friendly Cottage in the Countryside
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, (44 reviews)
"Cozy and clean. Enjoyed our stay. Kids loved that the park was so close!"
United States
Angie R.
The price is CA $208
CA $314 total
includes taxes & fees
Sep 8 - Sep 9
Park View Place 4 Blocks From the World's Biggest
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

4. 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, (66 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.
The price is CA $235
CA $349 total
includes taxes & fees
Sep 8 - Sep 9
Cottage By The Park Home of The Big Things
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, (6 reviews)
"Great off the beat cabin. Absolutely fell in love with the cabin itself and the location!!!! Maggie was awesome to talk too. Very pleasant- we will be back!"
United States
Jeremy
The price is CA $249
CA $298 total
includes taxes & fees
Sep 7 - Sep 8
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A brick house with a white door, a mailbox, and a wooden porch.

6. 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.
The price is CA $152
CA $249 total
includes taxes & fees
Sep 14 - Sep 15
Brickway Retreat
A tent set up on a wooden platform surrounded by trees.

7. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is CA $75
CA $109 total
includes taxes & fees
Sep 7 - Sep 8
Bell Tent Under the Stars
A modern kitchen with a brick wall, a bar area with stools, and a large island.

8. 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, (13 reviews)
"Beautiful, quiet, and comfortable! The hosts thought of everything you could ask for. Will definitely stay again the next time we are in town. "
United States
Amanda J.
The price is CA $163
CA $290 total
includes taxes & fees
Sep 13 - Sep 14
The Exchange. Downtown Luxury for Two, XCHNG. Industrial Executive Loft w/ King Bed
A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

9. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (12 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is CA $208
CA $274 total
includes taxes & fees
Sep 29 - Sep 30
Cozy 2BR Loft in Downtown Charleston, IL
A spacious living area with a large window, a television, and a dining table.

10. Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Neoga
The price is CA $187
CA $373 total
includes taxes & fees
Sep 7 - Sep 8
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
An open-plan office with exposed brick walls, wooden floors, and large windows.

11. The Exchange. Cozy Studio., XCHNG Studio

The Exchange. Cozy Studio., XCHNG Studio
Effingham
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful place, love the location. "
United States
Dawn K.
The price is CA $139
CA $246 total
includes taxes & fees
Sep 13 - Sep 14
The Exchange. Cozy Studio., XCHNG Studio
A bar area with a wooden ceiling and bar stools.

12. 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.
The price is CA $170
CA $300 total
includes taxes & fees
Sep 8 - Sep 9
The Exchange. Loft Living.
A spacious kitchen with a large island, exposed brick walls, and large windows offering views of the city.

13. 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, (25 reviews)
"Place is super nice, very close to everything in town "
United States
BK5000
The price is CA $256
CA $458 total
includes taxes & fees
Sep 7 - Sep 8
The Exchange. Big Luxury Loft, XCHNG. Modern Loft in the heart of Effingham.
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

Best Western Heartland Inn

Best Western Heartland Inn

10/10 Excellent
"The staff here is the best we’ve ever had anywhere. They are the most accommodating and nicest people we’ve met anywhere. Please give this place a try. Thank you for everything you did for us."
william 1-night trip
Posted 5 hours ago
Best Western Heartland Inn

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenup vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenup vacation rentals we have selected for you start as low as CA $109 per night. Entering your travel dates in the search wizard 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 Mailbox.

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.