Charleston Vacation Rentals

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Our top choices for Charleston vacation rentals

Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Charming A-frame cabin set in the woods overlooking deep wooded ravines.
Charleston
10.0 out of 10, Exceptional, (2 reviews)
"This was exactly what I was looking for. A few nights of campfire cooking - the quiet of the woods - a comfortable bed - What more could you want? Becca outdid every VRBO host with a welcoming attitude, coffee and pastries (and fresh eggs!) in the mornings - she even did my dishes so I wouldn’t have to spend my vacation time cleaning. Just a lovely stay for anyone looking for an unplugged, quiet weekend - camping but with a bed, a roof, and a helpful host. I definitely intend to be back soon. "
United States
MATTHEW B.
The price is CA $155
CA $253 total
includes taxes & fees
May 12 - May 13
Charming A-frame cabin set in the woods overlooking deep wooded ravines.

Bell Tent Under the Stars

Bell Tent Under the Stars
Charleston
The price is CA $74
CA $107 total
includes taxes & fees
May 17 - May 18
Bell Tent Under the Stars

Cozy 2BR Loft in Downtown Charleston, IL

Cozy 2BR Loft in Downtown Charleston, IL
Charleston
10.0 out of 10, Exceptional, (11 reviews)
"Cute little loft and great location in the main square with lots of walkable restaurants."
United States
Thomas
The price is CA $205
CA $271 total
includes taxes & fees
May 20 - May 21
Cozy 2BR Loft in Downtown Charleston, IL

Vintage Charmer on Main Street

Vintage Charmer on Main Street
Greenup
10.0 out of 10, Exceptional, (65 reviews)
"Host very kind and responsive, nice place to stay."
United States
JEREMY W.
The price is CA $121
CA $193 total
includes taxes & fees
May 21 - May 22
Vintage Charmer on Main Street

Prairieview Cabin - with Hot Tub

Prairieview Cabin - with Hot Tub
Sullivan
10.0 out of 10, Exceptional, (37 reviews)
"Great getaway! 2 adults relaxing and enjoyed the tranquility. Spacious and really enjoyed the porch and hot tub. "
United States
Ana Rosa R.
The price is CA $213
CA $362 total
includes taxes & fees
May 11 - May 12
Prairieview Cabin - with Hot Tub

Brickway Retreat

Brickway Retreat
Mattoon
9.8 out of 10, Exceptional, (46 reviews)
"It was a wonderful experience. The accommodations were perfect for our family of 7. It was so much better than booking multiple hotel rooms. "
United States
VINCENT
The price is CA $140
CA $235 total
includes taxes & fees
May 11 - May 12
Brickway Retreat

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, (43 reviews)
"Wonderful stay and a great location to all we wanted to see and do. Comfortable beds and cute furnishings too!"
United States
Stephanie G.
The price is CA $191
CA $294 total
includes taxes & fees
May 27 - May 28
Park View Place 4 Blocks From the World's Biggest

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, (61 reviews)
"Great house, very clean, host was very responsive and friendly! Would definitely recommend staying here! "
United States
Shawna L.
The price is CA $219
CA $328 total
includes taxes & fees
Jun 2 - Jun 3
Cottage By The Park Home of The Big Things

Prairieview Cottage Retreat - Hot Tub Sunsets

Prairieview Cottage Retreat - Hot Tub Sunsets
Sullivan
10.0 out of 10, Exceptional, (57 reviews)
"It was a wonderful stay. We loved the location and the patio during the evening!"
United States
Lyndsey C.
The price is CA $265
CA $491 total
includes taxes & fees
May 13 - May 14
Prairieview Cottage Retreat - Hot Tub Sunsets

Luxury Log Retreat with Hot Tub, Near Homestead & Winery

Luxury Log Retreat with Hot Tub, Near Homestead & Winery
Paris
9.4 out of 10, Exceptional, (10 reviews)
"The property was absolutely fantastic. Great host. We will be back."
United States
Mike R.
The price is CA $369
CA $655 total
includes taxes & fees
May 15 - May 16
Luxury Log Retreat with Hot Tub, Near Homestead & Winery

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Marshall
9.8 out of 10, Exceptional, (25 reviews)
"Everything was great! Well stocked and loved the back porch! "
United States
Kylie N.
The price is CA $340
CA $653 total
includes taxes & fees
May 15 - May 16
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH

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

Cozy, New 1-bedroom house on Lake Mattoon with dock, porch and stunning view.
Neoga
The price is CA $196
CA $379 total
includes taxes & fees
Jun 7 - Jun 8
Cozy, New 1-bedroom house on Lake Mattoon with dock, porch and stunning view.
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?

The Hideaway: This highly rated vacation home rental in Charleston has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.