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Holiday Rentals in Chickasaw County

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Our top choices for Chickasaw County holiday rentals

Fridge, microwave, oven, stovetop
game day weekend! charming 2-bedroom in meadowbrook.

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)
"Owner is very understanding, very responsive. Home is comfortable and plenty of room. "
United States
Kristina B.
The price is €258
includes taxes & fees
4 Jan - 5 Jan 2026
game day weekend! charming 2-bedroom in meadowbrook.
Outdoor dining
Charming 1940s Bungalow Cozy Vibes & Vintage Style

Charming 1940s Bungalow Cozy Vibes & Vintage Style

Charming 1940s Bungalow Cozy Vibes & Vintage Style
West Point
10.0 out of 10, Exceptional, (5)
"Very clean and nice neighborhood, will stay again "
United States
Brent P.
The price is €190
includes taxes & fees
14 Jan - 15 Jan 2026
Charming 1940s Bungalow Cozy Vibes & Vintage Style
TV
Fawn Grove cottage

Fawn Grove cottage

Fawn Grove cottage
Mantachie
The price is €177
includes taxes & fees
2 Jan - 3 Jan 2026
Fawn Grove cottage
Exterior
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6

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, (51)
"Comfortable cabin and beautiful surroundings!"
United States
Gary
The price is €245
includes taxes & fees
11 Jan - 12 Jan 2026
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Smart TV, fireplace
The Callaway Cottage- HOME AWAY FROM HOME!

The Callaway Cottage- HOME AWAY FROM HOME!

The Callaway Cottage- HOME AWAY FROM HOME!
Tupelo
9.4 out of 10, Exceptional, (19)
"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 €227
includes taxes & fees
1 Jan - 2 Jan 2026
The Callaway Cottage- HOME AWAY FROM HOME!
Exterior
Hollywood Bungalow

Hollywood Bungalow

Hollywood Bungalow
Tupelo
10.0 out of 10, Exceptional, (21)
"Very nice property with great eclectic furnishings. We loved our stay! We will book again!"
United States
Sandra
The price is €289
includes taxes & fees
4 Jan - 5 Jan 2026
Hollywood Bungalow
Property grounds
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

Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Belden
10.0 out of 10, Exceptional, (14)
"Perfect place! "
United States
April F.
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Fridge, microwave, oven, stovetop
The Duplex - 2bed/1bath duplex unit family & pet friendly

The Duplex - 2bed/1bath duplex unit family & pet friendly

The Duplex - 2bed/1bath duplex unit family & pet friendly
2.0 star property
West Point
The price is €182
includes taxes & fees
1 Jan - 2 Jan 2026
The Duplex - 2bed/1bath duplex unit family & pet friendly
Exterior
The Sugar Shack Cottage with Hot Tub

The Sugar Shack Cottage with Hot Tub

The Sugar Shack Cottage with Hot Tub
Tupelo
10.0 out of 10, Exceptional, (35)
"Hot tub area was very clean."
United States
Dalton W.
The price is €285
includes taxes & fees
1 Jan - 2 Jan 2026
The Sugar Shack Cottage with Hot Tub
Outdoor dining
Bristow Bungalow

Bristow Bungalow

Bristow Bungalow
Tupelo
9.2 out of 10, Wonderful, (32)
"It was so nice! I would definitely stay here again!"
United States
Abi H.
The price is €248
includes taxes & fees
4 Jan - 5 Jan 2026
Bristow Bungalow
Interior
Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi

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

Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
2.0 star property
Aberdeen
10.0 out of 10, Exceptional, (1)
"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 €261
includes taxes & fees
1 Jan - 2 Jan 2026
Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
Property grounds
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

Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Belden
10.0 out of 10, Exceptional, (8)
"The hosts was very pleasant to work with. We all a great stay and just enjoyed our downtime for our girls trip getaway. The cottage was clean and easy to locate."
United States
April C.
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Exterior
Spacious Historic Downtown home that sleeps up to 10!

Spacious Historic Downtown home that sleeps up to 10!

Spacious Historic Downtown home that sleeps up to 10!
Tupelo
10.0 out of 10, Exceptional, (62)
"Nice clean house with plenty of space. Quiet location with a nice outside space also. "
United States
Kathleen B.
The price is €295
includes taxes & fees
4 Jan - 5 Jan 2026
Spacious Historic Downtown home that sleeps up to 10!
Property grounds
Family Lake Glamping for an Outdoor Adventure in Tupelo, Mississippi

Family Lake Glamping for an Outdoor Adventure in Tupelo, Mississippi

Family Lake Glamping for an Outdoor Adventure in Tupelo, Mississippi
2.0 star property
Tupelo
The price is €153
includes taxes & fees
2 Jan - 3 Jan 2026
Family Lake Glamping for an Outdoor Adventure in Tupelo, Mississippi
Property grounds
Moon Lake

Moon Lake

Moon Lake
2.0 star property
Tupelo
The price is €152
includes taxes & fees
5 Jan - 6 Jan 2026
Moon Lake
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Pink House Social — Where We’re Unapologetically Pink and Undeniably Luxe.

Pink House Social — Where We’re Unapologetically Pink and Undeniably Luxe.

Pink House Social — Where We’re Unapologetically Pink and Undeniably Luxe.
2.0 star property
Amory
10.0 out of 10, Exceptional, (1)
"this house is so beautiful & the host was amazing! the theme & decor of the house is so girly & chic. i will definitely book again in the future!"
United States
danielle j.
The price is €497
includes taxes & fees
4 Jan - 5 Jan 2026
Pink House Social — Where We’re Unapologetically Pink and Undeniably Luxe.
Interior
Charming 2-bedroom house 20 miles from stadium

Charming 2-bedroom house 20 miles from stadium

Charming 2-bedroom house 20 miles from stadium
Oxford
The price is €454
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom house 20 miles from stadium
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

Comfort Inn Tupelo Central

Comfort Inn Tupelo Central

10/10 Excellent
"satisfied customer"
gwenita 1-night trip
Posted 2 days ago
Comfort Inn Tupelo Central

Find out more about Chickasaw County

Holiday Homes in Chickasaw County

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