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Charleston Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Charleston vacation rentals

Exterior

1. Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby

Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby
Crofton
9.8 out of 10, Exceptional, (187 reviews)
"Loved the cabin!! Will definitely rent again."
United States
Barbara
The price is SAR 375
SAR 656 total
includes taxes & fees
12 Aug - 13 Aug
Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby
Coffee/tea maker, fridge, microwave, oven

2. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY
Princeton
10.0 out of 10, Exceptional, (43 reviews)
"The Farmhouse exceeded my expectations in every way: comfort of furnishings, amenities, toiletries, fun welcome snacks and coffee selections, the beauty of the property, and the surrounding countryside- lovely- and the hosts were a pleasure to work with. "
United States
Nina H.
The price is SAR 422
SAR 702 total
includes taxes & fees
19 Aug - 20 Aug
Littlefield Farmhouse in Princeton, KY
Interior

3. Union Station Union Station

Union Station Union Station
Madisonville
9.4 out of 10, Exceptional, (6 reviews)
"Was a beautiful house and a lovey stay! "
United States
Rhonda P.
Union Station Union Station
Outdoor dining

4. Charming cabin with amazing views located on Toontucky Farms

Charming cabin with amazing views located on Toontucky Farms
White Plains
10.0 out of 10, Exceptional, (8 reviews)
" Stayed for a week very nice place. "
United States
Brandon L.
The price is SAR 413
SAR 627 total
includes taxes & fees
7 Sep - 8 Sep
Charming cabin with amazing views located on Toontucky Farms
Terrace/patio

5. Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.

Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.
Crofton
10.0 out of 10, Exceptional, (64 reviews)
"Great property! We will visit again!"
United States
Brie B.
The price is SAR 601
SAR 1,103 total
includes taxes & fees
12 Aug - 13 Aug
Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.
Exterior

6. Quaint cottage with 3 queen beds and screened porch.

Quaint cottage with 3 queen beds and screened porch.
Crofton
10.0 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again!"
United States
Becky S.
The price is SAR 657
SAR 1,172 total
includes taxes & fees
15 Aug - 16 Aug
Quaint cottage with 3 queen beds and screened porch.
Smart TV

7. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (27 reviews)
"Host was great to work with. House was very spacious and comfortable. Will definitely stay again."
United States
Beverly W.
The price is SAR 507
SAR 1,089 total
includes taxes & fees
13 Aug - 14 Aug
Lake Country House on City Square
Fireplace

8. Cozy Nook Retreat - Fireplace /Full Kitchen

Cozy Nook Retreat - Fireplace /Full Kitchen
Crofton
8.8 out of 10, Excellent, (3 reviews)
"Check In was very easy, the host was pleasant and very responsive, and house was clean."
United States
Jessica W.
The price is SAR 409
SAR 934 total
includes taxes & fees
10 Sep - 11 Sep
Cozy Nook Retreat - Fireplace /Full Kitchen
Game room

9. Great for Family Reunions, Hunting Lodge And Pet Friendly!

Great for Family Reunions, Hunting Lodge And Pet Friendly!
Crofton
9.8 out of 10, Exceptional, (127 reviews)
"We were there for a church retreat. The house was perfect for us. It was quiet and very peaceful. We hope to come again."
United States
Paula M.
The price is SAR 1,267
SAR 2,400 total
includes taxes & fees
12 Aug - 13 Aug
Great for Family Reunions, Hunting Lodge And Pet Friendly!
Private kitchen

10. Enjoy mama’s House in a quiet little area of Crofton ky

Enjoy mama’s House in a quiet little area of Crofton ky
Crofton
10.0 out of 10, Exceptional, (1 review)
"This house was clean and perfect for my family of 7. It is spacious, clean and so cute. We will definitely stay here again next time we are in the area."
United States
Mandy C.
The price is SAR 1,126
SAR 1,873 total
includes taxes & fees
12 Aug - 13 Aug
Enjoy mama’s House in a quiet little area of Crofton ky
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 Inn & Suites Madisonville

Comfort Inn & Suites Madisonville

10/10 Excellent
"They are remodeling some places that are a little outdated. Our room was spotless, just a bit outdated. The pool and hot tub were working perfectly and more updated than many other places. Breakfast had biscuits and gravy, bacon, mini omelets, cereal, pastries, all the good stuff. The gym was updated as well. Highly recommend."
margaret 1-night trip
Posted 5 hours ago
Comfort Inn & Suites Madisonville

Frequently asked questions

Can I find vacation rentals in Charleston?

Yes, there are vacation rentals close to well known sights in Charleston, or you can choose a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Charleston?

Littlefield Farmhouse in Princeton, KY: This vacation home rental outside of Charleston is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

What’s there to see and do in Charleston?

While you're exploring the area, Pennyrile Forest State Resort Park and Madisonville City Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Ruby Laffon Log Cabin and Gleam Mahr Center for Arts.

What’s a vacation rental in Charleston like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Charleston. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for small groups.