A wooden boardwalk through a swamp with tall trees and water.

Chickasaw County Holiday Rentals

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Our top choices for Chickasaw County holiday rentals

Coffee/tea maker, fridge, microwave, oven

1. Where Historic Charm Meets Comfortable Cottage Stays in Mississippi

Where Historic Charm Meets Comfortable Cottage Stays in Mississippi
Houston
The price is HK$3,131
HK$5,264 total
includes taxes & fees
15 Sept - 16 Sept
Where Historic Charm Meets Comfortable Cottage Stays in Mississippi
Exterior

2. Where Historic Charm Meets Comfortable Cottage Stays at The Oak in Mississippi

Where Historic Charm Meets Comfortable Cottage Stays at The Oak in Mississippi
Houston
The price is HK$3,131
HK$5,248 total
includes taxes & fees
15 Sept - 16 Sept
Where Historic Charm Meets Comfortable Cottage Stays at The Oak in Mississippi
Interior

3. Relax to the hum of alpacas just off the balcony of this former Amish store

Relax to the hum of alpacas just off the balcony of this former Amish store
Pontotoc
10.0 out of 10, Exceptional, (1 review)
"This was our Honeymoon. We found the place private and enjoyable. Highly recommend if you are just looking to get away."
United States
Jeffrey D.
The price is HK$989
HK$1,688 total
includes taxes & fees
18 Aug - 19 Aug
Relax to the hum of alpacas just off the balcony of this former Amish store
Terrace/patio

4. Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6

Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Mathiston
9.8 out of 10, Exceptional, (58 reviews)
"Comfortable cabin and beautiful surroundings!"
United States
Gary
The price is HK$1,165
HK$2,246 total
includes taxes & fees
18 Aug - 19 Aug
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Interior

5. Cozy 1-bedroom house in charming West Point with AC, WiFi

Cozy 1-bedroom house in charming West Point with AC, WiFi
West Point
9.6 out of 10, Exceptional, (24 reviews)
"Great property for a short stay."
United States
Ronnie R.
The price is HK$551
HK$841 total
includes taxes & fees
24 Aug - 25 Aug
Cozy 1-bedroom house in charming West Point with AC, WiFi
Interior

6. Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi

Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
Aberdeen
10.0 out of 10, Exceptional, (1 review)
"The Loft was a quaint cozy place to stay for the night. Me and my friends were attending the MS State/Vols game and was fortunate to find this place at the last minute. Ms. Danielle was a wonderful host and even let us check in early so we wouldn’t be late to the game. She also helped us promptly when we accidentally locked ourselves out of the Loft. Thank you Ms. Danielle for a wonderful stay!"
United States
Crystal D.
The price is HK$1,405
HK$2,343 total
includes taxes & fees
18 Aug - 19 Aug
Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
Smart TV

7. Charming 1940s Bungalow Cozy Vibes & Vintage Style

Charming 1940s Bungalow Cozy Vibes & Vintage Style
West Point
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and nice neighborhood, will stay again "
United States
Anonymous traveller
The price is HK$970
HK$1,894 total
includes taxes & fees
23 Aug - 24 Aug
Charming 1940s Bungalow Cozy Vibes & Vintage Style
Exterior

8. Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH

Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Belden
10.0 out of 10, Exceptional, (16 reviews)
"Everything was amazing! We will definitely be staying again. "
United States
Elizabeth N.
The price is HK$1,822
HK$2,099 total
includes taxes & fees
19 Aug - 20 Aug
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Exterior

9. Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH

Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Belden
10.0 out of 10, Exceptional, (9 reviews)
"Such a wonderful cottage to stay at during our thanksgiving trip to Tupelo, it was the perfect retreat after spending the day with family. Very clean, comfortable, and cozy. We will definitely stay again."
United States
Tim M.
The price is HK$1,822
HK$2,099 total
includes taxes & fees
18 Aug - 19 Aug
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Dining

10. game day weekend! charming 2-bedroom in meadowbrook.

game day weekend! charming 2-bedroom in meadowbrook.
West Point
10.0 out of 10, Exceptional, (2 reviews)
"Owner is very understanding, very responsive. Home is comfortable and plenty of room. "
United States
Kristina B.
The price is HK$904
HK$2,437 total
includes taxes & fees
18 Aug - 19 Aug
game day weekend! charming 2-bedroom in meadowbrook.
Interior

11. Modern Historic Family Retreat House in Downtown Tupelo

Modern Historic Family Retreat House in Downtown Tupelo
Tupelo
10.0 out of 10, Exceptional, (4 reviews)
"We had a absolutely wonderful stay at this property! The home was exceptionally clean, newly remodeled, and the layout was absolutely perfect for our family. It is situated right in downtown Tupelo, giving us the perfect balance of a quiet, peaceful stay while still being incredibly close to everything.The host was amazingly welcoming and went above and beyond, adding so many thoughtful, personalized touches for our family that made us feel right at home. It is an incredibly family-friendly...
United States
Jasmine W.
The price is HK$1,379
HK$3,087 total
includes taxes & fees
18 Aug - 19 Aug
Modern Historic Family Retreat House in Downtown Tupelo
Smart TV, DVD player

12. The Sugar Shack Cottage with Hot Tub

The Sugar Shack Cottage with Hot Tub
Tupelo
10.0 out of 10, Exceptional, (50 reviews)
"Nice clean place to stay in a convenient area"
United States
Evan D.
The price is HK$1,059
HK$2,559 total
includes taxes & fees
18 Aug - 19 Aug
The Sugar Shack Cottage with Hot Tub
Coffee/tea maker, fridge, microwave, oven

13. Bristow Bungalow

Bristow Bungalow
Tupelo
9.0 out of 10, Wonderful, (40 reviews)
"Just a great house! "
United States
Diane G.
The price is HK$1,295
HK$2,356 total
includes taxes & fees
10 Sept - 11 Sept
Bristow Bungalow
Fridge, microwave, oven, stovetop

14. Pink House Social

Pink House Social
Amory
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay in the Pink House. The owner was very easy to work with and we loved the decor. It was a perfect place for our group to stay for our first trip to Mississippi! "
Canada
Dorothy L.
The price is HK$1,797
HK$3,642 total
includes taxes & fees
24 Aug - 25 Aug
Pink House Social
Smart TV

15. Hollywood Bungalow

Hollywood Bungalow
Tupelo
10.0 out of 10, Exceptional, (37 reviews)
"Great stay! Very clean and comfortable!"
United States
Michelle A.
The price is HK$1,138
HK$3,030 total
includes taxes & fees
6 Sept - 7 Sept
Hollywood Bungalow
Coffee/tea maker, fridge, microwave, oven

16. The Callaway Cottage- HOME AWAY FROM HOME!

The Callaway Cottage- HOME AWAY FROM HOME!
Tupelo
9.4 out of 10, Exceptional, (25 reviews)
"Beautiful property in a great neighborhood!"
United States
Mary L.
The price is HK$1,138
HK$2,163 total
includes taxes & fees
30 Aug - 31 Aug
The Callaway Cottage- HOME AWAY FROM HOME!
Exterior

17. 1 King Bed | Non-Smoking, Hot Tub, Micfridge

1 King Bed | Non-Smoking, Hot Tub, Micfridge
Tupelo
10.0 out of 10, Exceptional, (134 reviews)
"Space was good for our group. We really appreciated having family rooms option."
United States
Anonymous traveller
The price is HK$914
HK$997 total
includes taxes & fees
23 Aug - 24 Aug
1 King Bed | Non-Smoking, Hot Tub, Micfridge
2 bedrooms, iron/ironing board, travel cot, free WiFi

18. The Duplex - 2 bedroom/1 bath, full kitchen duplex unit - family & pet friendly.

The Duplex - 2 bedroom/1 bath, full kitchen duplex unit - family & pet friendly.
West Point
The price is HK$1,256
HK$2,149 total
includes taxes & fees
18 Aug - 19 Aug
The Duplex - 2 bedroom/1 bath, full kitchen duplex unit - family & pet friendly.
Exterior

19. NEW DOWNTOWN TUPELO- HOUND DOG BUNGALOW -ROCK-N-ROLL themed 1BR 1B Shotgun style

NEW DOWNTOWN TUPELO- HOUND DOG BUNGALOW -ROCK-N-ROLL themed 1BR 1B Shotgun style
Tupelo
9.6 out of 10, Exceptional, (4 reviews)
"Clean and set up just for me and my dog. I enjoyed my stay and Mel was very helpful and kind. "
United States
Neesha O.
The price is HK$510
HK$1,582 total
includes taxes & fees
8 Sept - 9 Sept
NEW DOWNTOWN TUPELO- HOUND DOG BUNGALOW -ROCK-N-ROLL themed 1BR 1B Shotgun style
Exterior detail

20. Fawn Grove cottage

Fawn Grove cottage
Mantachie
10.0 out of 10, Exceptional, (3 reviews)
"It was great, clean, and exactly what we needed. However gps is incorrect about where the house is. The mailbox is not clearly marked and so it is hard to locate in the dark like we did. …. When you get directed to the vrbo by the cops, because you made it in late and cannot find it!"
United States
Laura p.
The price is HK$785
HK$1,587 total
includes taxes & fees
31 Aug - 1 Sept
Fawn Grove cottage
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 Chickasaw County Hotel Reviews

Best Western Plus Tupelo Inn & Suites

Best Western Plus Tupelo Inn & Suites

10/10 Excellent
"This was a very nice property in a great location close to restaurants and shopping. The staff were very nice and accommodating. The rooms are clean and the bed was so comfortable. The property itself is very well kept if I’m ever in Tupelo Mississippi again, I will definitely stay here!"
Teresa 1-night trip
Posted 6 hours ago
Best Western Plus Tupelo Inn & Suites