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

Charleston 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 Charleston vacation rentals

Coffee/tea maker, fridge, microwave, oven

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 ￥23,969
￥32,008 total
includes taxes & fees
Oct 1 - Oct 2
Cozy 2BR Loft in Downtown Charleston, IL
Property grounds

2. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is ￥8,629
￥12,533 total
includes taxes & fees
Sep 2 - Sep 3
Bell Tent Under the Stars
Exterior detail

3. Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (52 reviews)
"Great place for a stay. Nice amenities and very clean. Would absolutely stay again"
United States
Kevin F.
The price is ￥17,577
￥29,128 total
includes taxes & fees
Sep 9 - Sep 10
Brickway Retreat
Interior

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 ￥14,093
￥22,557 total
includes taxes & fees
Sep 3 - Sep 4
Vintage Charmer on Main Street
Smart TV

5. 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 ￥23,969
￥36,747 total
includes taxes & fees
Sep 2 - Sep 3
Park View Place 4 Blocks From the World's Biggest
Smart TV, fireplace

6. 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 ￥27,164
￥40,642 total
includes taxes & fees
Sep 2 - Sep 3
Cottage By The Park Home of The Big Things
Terrace/patio

7. 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 ￥21,715
￥39,779 total
includes taxes & fees
Sep 15 - Sep 16
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
Coffee/tea maker, fridge, microwave, oven

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, (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 ￥28,762
￥34,716 total
includes taxes & fees
Sep 2 - Sep 3
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
Smart TV, fireplace

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 ￥24,955
￥42,390 total
includes taxes & fees
Sep 2 - Sep 3
Prairieview Cabin - with Hot Tub
TV

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 ￥21,596
￥43,377 total
includes taxes & fees
Sep 2 - Sep 3
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
Interior

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 ￥32,981
￥61,083 total
includes taxes & fees
Sep 15 - Sep 16
Prairieview Cottage Retreat - Hot Tub Sunsets
Dining

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 ￥39,788
￥77,222 total
includes taxes & fees
Sep 2 - Sep 3
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Smart TV, fireplace

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 ￥43,143
￥77,391 total
includes taxes & fees
Sep 10 - Sep 11
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

Baymont by Wyndham Tuscola

Baymont by Wyndham Tuscola

10/10 Excellent
"We like the location. Close to friends."
Mark 1-night trip
Posted 17 hours ago
Baymont by Wyndham Tuscola

Find out more about Charleston

Search for holiday rentals in Charleston on Expedia! You can easily find your home rentals, villas, holiday apartments in Charleston using one of the methods below:

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Look no further and take a look at our great range of rental properties in Charleston!

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.