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

Interior

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, (23 reviews)
"Very quaint and quiet home. Communication with host was good and they were helpful when needed. "
United States
Brenda
The price is HK$551
HK$841 total
includes taxes & fees
10 Jul - 11 Jul
Cozy 1-bedroom house in charming West Point with AC, WiFi
Terrace/patio

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, (56 reviews)
"Comfortable cabin and beautiful surroundings!"
United States
Gary
The price is HK$1,165
HK$2,211 total
includes taxes & fees
3 Jul - 4 Jul
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Exterior detail

Fawn Grove cottage

Fawn Grove cottage
Mantachie
10.0 out of 10, Exceptional, (2 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$784
HK$1,553 total
includes taxes & fees
27 Jul - 28 Jul
Fawn Grove cottage
Smart TV

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$969
HK$1,876 total
includes taxes & fees
15 Jul - 16 Jul
Charming 1940s Bungalow Cozy Vibes & Vintage Style
Interior

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
The price is HK$889
HK$1,573 total
includes taxes & fees
6 Jul - 7 Jul
Relax to the hum of alpacas just off the balcony of this former Amish store
Exterior

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, (8 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$1,821
HK$2,098 total
includes taxes & fees
6 Jul - 7 Jul
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Exterior

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$1,821
HK$2,098 total
includes taxes & fees
6 Jul - 7 Jul
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Smart TV, DVD player

The Sugar Shack Cottage with Hot Tub

The Sugar Shack Cottage with Hot Tub
Tupelo
10.0 out of 10, Exceptional, (46 reviews)
"The Sugar Shack Cottage was a very restful stop for us. It is decorated in a fun eclectic fashion that we really enjoyed. It was well-stocked and the beds were really comfortable. I highly recommend this for a chance to get rested and recharged. I really appreciated the charging ports for our devices and the Keurig coffeemaker. We didn't get a chance to use the hot tub."
United States
Kim
The price is HK$1,059
HK$2,465 total
includes taxes & fees
28 Jul - 29 Jul
The Sugar Shack Cottage with Hot Tub
Dining

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$960
HK$2,479 total
includes taxes & fees
15 Jul - 16 Jul
game day weekend! charming 2-bedroom in meadowbrook.
Smart TV

Hollywood Bungalow

Hollywood Bungalow
Tupelo
10.0 out of 10, Exceptional, (34 reviews)
"Great stay! Very clean and comfortable!"
United States
Michelle A.
The price is HK$1,137
HK$2,961 total
includes taxes & fees
2 Aug - 3 Aug
Hollywood Bungalow
Exterior

1 King Bed | Smoking, Micfridge

1 King Bed | Smoking, Micfridge
Tupelo
10.0 out of 10, Exceptional, (18 reviews)
The price is HK$525
HK$573 total
includes taxes & fees
5 Jul - 6 Jul
1 King Bed | Smoking, Micfridge
Golf

Old Waverly Golf Course Condo

Old Waverly Golf Course Condo
West Point
10.0 out of 10, Exceptional, (2 reviews)
"We’ll be staying there again!"
United States
Jeremiah G.
The price is HK$1,961
HK$3,776 total
includes taxes & fees
15 Jul - 16 Jul
Old Waverly Golf Course Condo
Fridge, microwave, oven, stovetop

The Callaway Cottage- HOME AWAY FROM HOME!

The Callaway Cottage- HOME AWAY FROM HOME!
Tupelo
9.4 out of 10, Exceptional, (23 reviews)
"This home is located in a very quiet neighborhood yet it is close enough to anything you want or need to do in Tupelo.We were able to relax and unwind after visiting with family and doing some shopping."
United States
Jonathan H.
The price is HK$953
HK$1,914 total
includes taxes & fees
5 Jul - 6 Jul
The Callaway Cottage- HOME AWAY FROM HOME!
Exterior

Spacious Historic Downtown home that sleeps up to 10!

Spacious Historic Downtown home that sleeps up to 10!
Tupelo
9.8 out of 10, Exceptional, (70 reviews)
"Great property in a great location!"
United States
Gary A.
The price is HK$1,405
HK$2,617 total
includes taxes & fees
6 Jul - 7 Jul
Spacious Historic Downtown home that sleeps up to 10!
Interior

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$2,342 total
includes taxes & fees
6 Jul - 7 Jul
Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
Interior

Modern Historic Family Retreat House in Downtown Tupelo

Modern Historic Family Retreat House in Downtown Tupelo
Tupelo
10.0 out of 10, Exceptional, (2 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$1,306
HK$2,839 total
includes taxes & fees
6 Jul - 7 Jul
Modern Historic Family Retreat House in Downtown Tupelo
Fridge, microwave, oven, stovetop

Bristow Bungalow

Bristow Bungalow
Tupelo
9.2 out of 10, Wonderful, (36 reviews)
"Just a great house! "
United States
Diane G.
The price is HK$1,294
HK$2,347 total
includes taxes & fees
8 Jul - 9 Jul
Bristow Bungalow
2 bedrooms, iron/ironing board, travel cot, free WiFi

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$1,176
HK$2,031 total
includes taxes & fees
15 Jul - 16 Jul
The Duplex - 2 bedroom/1 bath, full kitchen duplex unit - family & pet friendly.
Fridge, microwave, oven, stovetop

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$1,867
HK$3,727 total
includes taxes & fees
7 Jul - 8 Jul
Pink House Social
Exterior

2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Tupelo
10.0 out of 10, Exceptional, (18 reviews)
The price is HK$524
HK$572 total
includes taxes & fees
10 Jul - 11 Jul
2 Full Beds | Non-Smoking, Micfridge
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

Hotel Tupelo, a Wyndham Hotel

Hotel Tupelo, a Wyndham Hotel

10/10 Excellent
"Excellent stay - looking forward to our next visit"
Moira Colleen 1-night trip
Posted 1 hour ago
Hotel Tupelo, a Wyndham Hotel