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Charleston Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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 ￥15,831
￥27,655 total
includes taxes & fees
Oct 14 - Oct 15
Lakeside Cottage, Fishing, Canoe & Kayak, Pet Friendly, Golf and Hiking Nearby
A bathroom with a vanity, a mirror, a sink, a towel rack, and a window with a view of a garden.

2. 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.
The price is ￥14,131
￥50,503 total
includes taxes & fees
Oct 18 - Oct 19
Union Station Union Station
An open-plan living area with a sofa, two armchairs, a ceiling fan, and a door leading to a balcony.

3. 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 ￥14,160
￥59,069 total
includes taxes & fees
Oct 14 - Oct 15
Loop Haven is an awesome place to stay.
Living area

4. 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 ￥9,341
￥29,252 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Nook Retreat - Fireplace /Full Kitchen
A wooden deck with a table and chairs, overlooking a grassy field and a sunset.

5. 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 ￥17,414
￥26,430 total
includes taxes & fees
Oct 20 - Oct 21
Charming cabin with amazing views located on Toontucky Farms
A covered porch with wooden railings, a patterned rug, and a view of a wooded area.

6. 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 ￥25,330
￥48,396 total
includes taxes & fees
Oct 20 - Oct 21
Cozy 2-bedroom cabin nestled in the woods adjoining Pennyrile Forest State Park.
A room with wooden paneling, a brown leather sofa, and a door leading to another room.

7. The Nisbet Nest The Nisbet Nest

The Nisbet Nest The Nisbet Nest
Madisonville
6.0 out of 10, (1 review)
The price is ￥19,662
￥61,864 total
includes taxes & fees
Nov 2 - Nov 3
The Nisbet Nest The Nisbet Nest
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 ￥21,372
￥45,899 total
includes taxes & fees
Oct 14 - Oct 15
Lake Country House on City Square
Exterior

9. 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, (96 reviews)
"Would definitely stay here again!"
United States
Becky S.
The price is ￥27,762
￥49,535 total
includes taxes & fees
Oct 20 - Oct 21
Quaint cottage with 3 queen beds and screened porch.
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 ￥53,541
￥101,411 total
includes taxes & fees
Oct 14 - Oct 15
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 ￥47,592
￥79,153 total
includes taxes & fees
Oct 14 - Oct 15
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

Quaint cottage with 3 queen beds and screened porch.

Quaint cottage with 3 queen beds and screened porch.

10/10 Excellent
"We enjoyed our stay immensely. It was great to relax and disconnect for a week. The cabin had everything we could possibly need."
Jennifer Z. 7-night trip
Posted 5 days ago
Quaint cottage with 3 queen beds and screened porch.

Find out more about Charleston

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

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.