A castle-like building with a tall tower, traffic lights, and a crosswalk.

Charleston Holiday Rentals

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Our top choices for Charleston holiday rentals

1. 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 NZ$331
includes taxes & fees
29 Sept - 30 Sept
Cozy 2BR Loft in Downtown Charleston, IL

2. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is NZ$133
includes taxes & fees
31 Aug - 1 Sept
Bell Tent Under the Stars

3. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (51 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is NZ$305
includes taxes & fees
31 Aug - 1 Sept
Brickway Retreat

4. 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 NZ$239
includes taxes & fees
31 Aug - 1 Sept
Vintage Charmer on Main Street

5. The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
Arthur
The price is NZ$388
includes taxes & fees
14 Sept - 15 Sept
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood

6. 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 NZ$364
includes taxes & fees
31 Aug - 1 Sept
Park View Place 4 Blocks From the World's Biggest

7. 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 NZ$405
includes taxes & fees
31 Aug - 1 Sept
Cottage By The Park Home of The Big Things

8. 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, (5 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 NZ$364
includes taxes & fees
31 Aug - 1 Sept
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL

9. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is NZ$444
includes taxes & fees
2 Sept - 3 Sept
Prairieview Cabin - with Hot Tub

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 NZ$455
includes taxes & fees
31 Aug - 1 Sept
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

11. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (61 reviews)
"Very nice everything was perfect couldn't have asked for a better time recommend very much"
United States
Ben D.
The price is NZ$643
includes taxes & fees
21 Sept - 22 Sept
Prairieview Cottage Retreat - Hot Tub Sunsets

12. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (28 reviews)
"We had a blast!!! Thank you!!!"
United States
Theresa
The price is NZ$806
includes taxes & fees
31 Aug - 1 Sept
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

13. Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.6 out of 10, Exceptional, (14 reviews)
"Knowing we were checking in to a log cabin, we were not expecting it to be so clean and nice! The cabin is spacious, with plenty of comfortable seating, as well as lots of work space and storage, especially in the kitchen. The place seems to be new and is well cared for. Loved the setting! It is a beautiful, wooded property with plenty of privacy, but yet only 15-20 minutes from town. We enjoyed our stay very much!"
United States
Barbara A.
The price is NZ$810
includes taxes & fees
31 Aug - 1 Sept
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
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 Charleston Hotel Reviews

Find out more about Charleston

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Charleston holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Charleston. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Charleston. Seeing all the best attractions is bound to make you fall in love with Charleston. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Charleston short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Charleston?

Yes, there are holiday rentals in Charleston close to Doudna Fine Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Charleston is known for its university setting and sporting events. Make sure you have time to check out the live music and entertainment choices during your trip.

What are some of the best holiday rentals that Charleston has to offer?

Paradise Found in Illinois: This holiday home rental outside of Charleston is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Charleston?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Charleston stay.

What’s there to see and do in Charleston?

Explore the area and family-friendly sights such as Beachy's Bulk Foods, or get out into nature at a spot like Mattoon Peterson Park. While here, Fox Ridge State Park and Doudna Fine Arts Center are other places worth a visit.

What’s a holiday rental in Charleston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charleston. Holiday rentals offer amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.