Default HTG hotel image

Charleston Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Charleston vacation rentals

A small cabin with a porch, surrounded by trees and gravel.

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, (198 reviews)
"Loved the cabin!! Will definitely rent again."
United States
Barbara
The price is SAR 375
SAR 656 total
includes taxes & fees
1 Oct - 2 Oct
Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby
A spacious dining area with a large wooden table and chairs, a kitchen with white cabinets, and a ceiling with wooden beams.

2. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY
Princeton
10.0 out of 10, Exceptional, (44 reviews)
"Great place to stay! The house was spotless and very comfortable. The hosts were great. We will definitely be returning for another stay!"
United States
Beverly W.
The price is SAR 422
SAR 702 total
includes taxes & fees
1 Oct - 2 Oct
Littlefield Farmhouse in Princeton, KY
A wooden deck with a table and chairs, overlooking a grassy field and a sunset.

3. Charming cabin with amazing views located on Toontucky Farms

Charming cabin with amazing views located on Toontucky Farms
White Plains
9.8 out of 10, Exceptional, (9 reviews)
" Stayed for a week very nice place. "
United States
Brandon L.
The price is SAR 413
SAR 627 total
includes taxes & fees
13 Oct - 14 Oct
Charming cabin with amazing views located on Toontucky Farms
An open-plan living area with a sofa, two armchairs, a ceiling fan, and a door leading to a balcony.

4. Loop Haven is an awesome place to stay.

Loop Haven is an awesome place to stay.
Madisonville
9.4 out of 10, Exceptional, (14 reviews)
"Nice clean space with room for everything we needed. Host was quick to always keep us up to date on our reservation, check in and check out.One minor issue was resolved immediately. Would stay here again although it's not fenced in on one side so luckily that was not an issue for us."
United States
Dianne K.
The price is SAR 335
SAR 1,398 total
includes taxes & fees
2 Oct - 3 Oct
Loop Haven is an awesome place to stay.
A covered porch with wooden railings, a patterned rug, and a view of a wooded area.

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, (68 reviews)
"The place was very quiet and peaceful. I really enjoyed the calm atmosphere. It was a great place to relax and enjoy some peace and quiet. Everything was clean and comfortable, and I had a very nice stay."
United States
Anahyte
The price is SAR 601
SAR 1,099 total
includes taxes & fees
2 Oct - 3 Oct
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, (93 reviews)
"Would definitely stay here again!"
United States
Becky S.
The price is SAR 657
SAR 1,172 total
includes taxes & fees
1 Oct - 2 Oct
Quaint cottage with 3 queen beds and screened porch.
A bathroom with a vanity, a mirror, a sink, a towel rack, and a window with a view of a garden.

7. 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
A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

8. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (29 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 1,084 total
includes taxes & fees
13 Oct - 14 Oct
Lake Country House on City Square
Living area

9. 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 339
SAR 842 total
includes taxes & fees
5 Oct - 6 Oct
Cozy Nook Retreat - Fireplace /Full Kitchen
A cozy living room with a pool table, comfortable seating, and a staircase.

10. 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, (128 reviews)
"We had a wonderful stay at this property! The home was exactly as described. The host was responsive, friendly, and made the entire process seamless from booking through checkout."
United States
Delia G.
The price is SAR 1,267
SAR 2,400 total
includes taxes & fees
1 Oct - 2 Oct
Great for Family Reunions, Hunting Lodge And Pet Friendly!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

11. 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, (2 reviews)
"This place is perfect with a good view and a great location"
United States
Dalton D.
The price is SAR 1,126
SAR 1,874 total
includes taxes & fees
1 Oct - 2 Oct
Enjoy mama’s House in a quiet little area of Crofton ky
A two-story building with a covered porch and a small staircase.

12. Nice and Quite place to stay

Nice and Quite place to stay
Madisonville
The price is SAR 282
SAR 1,370 total
includes taxes & fees
1 Oct - 2 Oct
Nice and Quite place to stay
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charleston Hotel Reviews

Holiday Inn Express & Suites Madisonville by IHG

Holiday Inn Express & Suites Madisonville by IHG

10/10 Excellent
"Everything was clean, well thought out and worked perfectly. Breakfast was delicious and generous hours."
Teresa K 2-night trip
Posted 18 hours ago
Holiday Inn Express & Suites Madisonville by IHG

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 Madisonville Country Club and Ruby Laffon Log Cabin.

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.