Charleston Vacation Rentals

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Charleston vacation homes

A hot tub in an outdoor setting with a wooden deck and lounge chairs.

1. Perfect Couples Retreat - firepit

Perfect Couples Retreat - firepit
Carlisle County
10.0 out of 10, Exceptional, (1 review)
"This is such a quaint unique property. The host was very responsive and communicative. Highly recommend"
United States
Russell
The price is CA $179
CA $260 total
includes taxes & fees
Nov 28 - Nov 29
Perfect Couples Retreat - firepit
A hot tub with a wooden deck and outdoor seating area.

2. The Roost | Hot Tub, Ponds & Farm Views

The Roost | Hot Tub, Ponds & Farm Views
Carlisle County
The price is CA $202
CA $285 total
includes taxes & fees
Nov 12 - Nov 13
The Roost | Hot Tub, Ponds & Farm Views
A living room with a TV, a fireplace, a sofa, and wall art.

3. Little Blue Cottage on Spanish

Little Blue Cottage on Spanish
Cape Girardeau
8.4 out of 10, Very good, (59 reviews)
"Great cute place. "
United States
Jeremy W.
The price is CA $114
CA $141 total
includes taxes & fees
Nov 12 - Nov 13
Little Blue Cottage on Spanish
A modern kitchen with a built-in microwave, stainless steel appliances, and a sink.

4. Charming Home just minutes from Interstate and Mall

Charming Home just minutes from Interstate and Mall
Kevil
10.0 out of 10, Exceptional, (26 reviews)
"Location was great. Beds were so comfortable, place was so clean and nice. Very cute place to stay. Would stay here again!"
United States
Deannena H.
The price is CA $155
CA $266 total
includes taxes & fees
Nov 22 - Nov 23
Charming Home just minutes from Interstate and Mall
A kitchen with grey cabinets, a stainless steel dishwasher, a microwave, and an oven.

5. Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals

Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals
Cape Girardeau
The price is CA $149
CA $258 total
includes taxes & fees
Nov 30 - Dec 1
Cozy 2-bedroom house in tranquil Cape Girardeau, close to Semo & Hospitals
A single-story house with a gabled roof, a front porch with two chairs, and a front door with a decorative glass panel.

6. Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!

Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
New Madrid
10.0 out of 10, Exceptional, (1 review)
"The host was very quick to respond and so great to work with for on our stay. "
United States
Jessica S.
The price is CA $282
CA $499 total
includes taxes & fees
Nov 12 - Nov 13
Spacious 3-bedroom 2 story house in New Madrid near boat ramp with a toy room!
A two-story house with a front porch, a small garden, and a white picket fence.

7. 3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool

3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
Cape Girardeau
8.8 out of 10, Excellent, (46 reviews)
"Will definitely book again! Great location, comfortable stay."
United States
Pynktoria !.
The price is CA $253
CA $427 total
includes taxes & fees
Nov 12 - Nov 13
3+ acre Home: Pool Table, Putt-Putt, 4 miles to Downtown and SEMO, Summer Pool
A modern kitchen with white cabinetry, stainless steel appliances, and a window with a view of greenery.

8. Quiet Country Stay: Modern Home Near Paducah

Quiet Country Stay: Modern Home Near Paducah
Cunningham
8.4 out of 10, Very good, (5 reviews)
"Host was great. "
United States
Sheila C.
The price is CA $154
CA $401 total
includes taxes & fees
Nov 23 - Nov 24
Quiet Country Stay: Modern Home Near Paducah
A house with a backyard swimming pool, outdoor furniture, and a barbecue area.

9. 4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More

4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More
Cape Girardeau
9.8 out of 10, Exceptional, (11 reviews)
"Nice place, great times"
United States
Jace W.
The price is CA $507
CA $782 total
includes taxes & fees
Nov 12 - Nov 13
4-Bedroom Home - 2 King Beds, Summer Pool, Pool Table, Air Hockey + More
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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Learn more about Charleston

Quaint Charleston is calling! Discover its opera, entertainment, cathedral, and more.

See all hotels in Charleston
A sunset over a calm lake with tall trees reflected in the water.

Top reviews in Charleston

An indoor swimming pool with a 3 FT depth marker, a metal ladder, and a tiled floor.
Drury Inn & Suites Sikeston, MO

Drury Inn & Suites Sikeston, MO

Drury Inn & Suites Sikeston, MO
Sikeston

10/10 Excellent

Manager’s reception is a hit!
Canada
Thomas R
Reviewed April 29, 2026
Drury Inn & Suites Sikeston, MO

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