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

Charleston Vacation Rentals

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Our top choices for Charleston vacation 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 CA $206
CA $273 total
includes taxes & fees
Aug 27 - Aug 28
Cozy 2BR Loft in Downtown Charleston, IL

2. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is CA $74
CA $108 total
includes taxes & fees
Aug 24 - Aug 25
Bell Tent Under the Stars

3. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (51 reviews)
"Place wa exactly as described and the owner was a great communicator. Highly recommend this place and when we return will see if it’s available ! "
United States
Angela C.
The price is CA $151
CA $248 total
includes taxes & fees
Aug 24 - Aug 25
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 CA $121
CA $194 total
includes taxes & fees
Aug 24 - Aug 25
Vintage Charmer on Main Street

5. 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 $220
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
Cottage By The Park Home of The Big Things

6. 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 CA $248
CA $296 total
includes taxes & fees
Aug 25 - Aug 26
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL

7. 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 $193
CA $296 total
includes taxes & fees
Aug 24 - Aug 25
Park View Place 4 Blocks From the World's Biggest

8. 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 $186
CA $371 total
includes taxes & fees
Aug 24 - Aug 25
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!

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 CA $214
CA $363 total
includes taxes & fees
Sep 2 - Sep 3
Prairieview Cabin - with Hot Tub

10. 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 CA $343
CA $662 total
includes taxes & fees
Aug 24 - Aug 25
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

11. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (61 reviews)
"Very clean and cute place! We enjoyed our stay very much. The hosts were wonderful, and we even got the blessing of a visit by the 2 puppies that live on the property. Definitely recommend staying here! "
United States
Lisa S.
The price is CA $283
CA $522 total
includes taxes & fees
Sep 15 - Sep 16
Prairieview Cottage Retreat - Hot Tub Sunsets

12. 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 CA $372
CA $664 total
includes taxes & fees
Aug 24 - Aug 25
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Charleston?

Yes, you can find vacation rentals in Charleston close to Doudna Fine Arts Center, or you can go with a more secluded option if you'd like a relaxing place to 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 vacation rentals in Charleston?

Paradise Found in Illinois: Visitors like this Charleston vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill 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 vacation with amenities like a selection of games.

How many vacation rentals are there in Charleston?

With 3 Expedia vacation rentals, you're sure 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 vacation rental in Charleston like?

A vacation rental is a private property you can book for several days or longer in Charleston. Vacation rentals provide amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for family gatherings.