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

Charleston Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Charleston holiday rentals

A modern kitchen with a round dining table, chairs, a potted orchid, and a stainless steel refrigerator.

1. Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (13 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is HK$1,176
HK$1,546 total
includes taxes & fees
29 Sept - 30 Sept
Cozy 2BR Loft in Downtown Charleston, IL
A tent set up on a wooden platform surrounded by trees.

2. Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is HK$424
HK$490 total
includes taxes & fees
27 Sept - 28 Sept
Bell Tent Under the Stars
A brick house with a white door, a mailbox, and a wooden porch.

3. 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 HK$863
HK$1,413 total
includes taxes & fees
12 Oct - 13 Oct
Brickway Retreat
A wooden cabin entrance with a welcome sign, a small table with a lamp and flowers, and a woven mat on the floor.

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 HK$692
HK$1,107 total
includes taxes & fees
27 Sept - 28 Sept
Vintage Charmer on Main Street
A modern living room with two leather sofas, a dining area, and a kitchen in the background.

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, (68 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 HK$1,333
HK$1,945 total
includes taxes & fees
24 Oct - 25 Oct
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.

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, (45 reviews)
"Cozy and clean. Enjoyed our stay. Kids loved that the park was so close!"
United States
Angie R.
The price is HK$1,176
HK$1,779 total
includes taxes & fees
28 Sept - 29 Sept
Park View Place 4 Blocks From the World's Biggest
A modern kitchen with dark cabinets, stainless steel appliances, and a granite countertop.

7. 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, (8 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 HK$1,412
HK$1,687 total
includes taxes & fees
1 Oct - 2 Oct
Built 2025-"OUR NECK OF THE WOODS" close to all the BIG THINGS in Casey, IL
A small, rustic building with a metal roof, a porch with two chairs, and a gravel driveway.

8. 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
The price is HK$2,000
HK$3,287 total
includes taxes & fees
25 Sept - 26 Sept
Family Friendly Cottage in the Countryside
A small, cozy bedroom with a bed, pillows, and a striped rug.

9. 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 HK$854
HK$1,703 total
includes taxes & fees
12 Oct - 13 Oct
The Guest House by The Trestle, Quaint and Cozy cabin made with reclaimed wood
A cozy cabin interior with a wooden staircase, a fireplace, a Christmas tree, and a leather sofa.

10. 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, (15 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 HK$2,118
HK$3,749 total
includes taxes & fees
27 Sept - 28 Sept
Luxury Log Retreat with Hot Tub, Near Homestead & Winery
A covered outdoor seating area with a glass table, cushioned chairs, and a sofa.

11. FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (29 reviews)
"The house was clean and stocked with everything we needed for our 2 night stay. Beds were comfortable. Host was very quick to answer questions."
United States
Melani S.
The price is HK$1,953
HK$3,740 total
includes taxes & fees
1 Oct - 2 Oct
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.

12. Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (44 reviews)
"Very nice place to stay!"
United States
Brandon R.
The price is HK$1,290
HK$2,061 total
includes taxes & fees
5 Oct - 6 Oct
Prairieview Cabin - with Hot Tub
A spacious living area with a large window, a television, and a dining table.

13. 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 HK$1,060
HK$2,129 total
includes taxes & fees
5 Oct - 6 Oct
Cozy! 1-bedroom house on Lake Mattoon with dock, porch and stunning view!
A modern kitchen with a central island, dark cabinetry, and a ceiling fan.

14. Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (62 reviews)
"Very nice everything was perfect couldn't have asked for a better time recommend very much"
United States
Ben D.
The price is HK$1,653
HK$3,024 total
includes taxes & fees
5 Oct - 6 Oct
Prairieview Cottage Retreat - Hot Tub Sunsets
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

Comfort Suites Mattoon East

Comfort Suites Mattoon East

8/10 Good
"The layout of the room with the sink outside of the restroom was a bit weird"
Wanda 2-night trip
Posted 9 hours ago
Comfort Suites Mattoon East

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:

  • View our selection of featured holiday rentals in Charleston
  • Use the map to find apartments and other holiday homes in the Charleston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Charleston while they last

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

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?

Prairieview Cabin - with Hot Tub: This holiday home rental outside of Charleston offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 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.