Chickasaw County Vacation Rentals from ￥10,628: Search Short-Term Rentals

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

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Our top choices for Chickasaw County vacation rentals

A white door with a glass panel, a black doorbell, a welcome mat, and two potted plants.

1. Where Historic Charm Meets Comfortable Cottage Stays in Mississippi

Houston

￥100,397 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a bed, bedside tables, a nightstand, a window with blinds, and a wall-mounted artwork.

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

Houston

￥105,619 total

includes taxes & fees

Oct 5 - Oct 6

A kitchen with a double sink, a window with a view of trees and a roof, and a wooden countertop.

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

West Point

Ronnie R.

￥16,878 total

includes taxes & fees

Oct 4 - Oct 5

A room with wooden flooring, a ceiling fan, a TV mounted on the wall, a wooden entertainment unit, a staircase, and a door.

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

Pontotoc

Jeffrey D.

￥33,858 total

includes taxes & fees

Oct 12 - Oct 13

A dining area with a wooden table and chairs, a blue armchair, and a painting on the wall.

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

Aberdeen

"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!"

Crystal D.

￥50,552 total

includes taxes & fees

Oct 4 - Oct 5

A wooden deck with a railing, overlooking a forested area and a body of water.

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

Mathiston

Gary

￥44,387 total

includes taxes & fees

Oct 4 - Oct 5

A living room with a brown sofa, a blue armchair, a round coffee table, and a patterned rug.

7. Charming 1940s Bungalow Cozy Vibes & Vintage Style

West Point

Anonymous traveler

￥38,863 total

includes taxes & fees

Oct 4 - Oct 5

A living room with a brown leather sofa, a green armchair, a wooden coffee table, and a cowhide rug.

8. The Sugar Shack Cottage with Hot Tub

Tupelo

Evan D.

￥60,953 total

includes taxes & fees

Oct 5 - Oct 6

A hotel entrance with a covered walkway, a bench, and a parking area.

9. 1 King Bed | Non-Smoking, Micfridge

Tupelo

Anonymous traveler

￥10,628 total

includes taxes & fees

Oct 4 - Oct 5

A kitchen with white cabinets, stainless steel appliances, a wooden island with chairs, and a ceiling light fixture.

10. The Callaway Cottage- HOME AWAY FROM HOME!

Tupelo

Mary L.

￥40,103 total

includes taxes & fees

Oct 5 - Oct 6

A cabin-style building with a central open area, surrounded by a forest.

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

Belden

Tim M.

￥42,114 total

includes taxes & fees

Oct 5 - Oct 6

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

Belden

Elizabeth N.

￥42,114 total

includes taxes & fees

Oct 5 - Oct 6

A modern living room with a sofa, a coffee table with a bowl of pinecones and flowers, a lamp, and a view of the outdoors through large windows.

13. Modern Historic Family Retreat House in Downtown Tupelo

Tupelo

"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...

Jasmine W.

￥62,812 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with a marble countertop, stainless steel appliances, and wooden flooring.

14. Bristow Bungalow

Tupelo

Sam T.

￥43,647 total

includes taxes & fees

Oct 4 - Oct 5

A modern kitchen with a central island, stainless steel appliances, and a bar area with stools.

15. Pink House Social

Amory

Dorothy L.

￥69,764 total

includes taxes & fees

Oct 5 - Oct 6

16. Hollywood Bungalow

Tupelo

Jaşmíné B.

￥60,086 total

includes taxes & fees

Oct 5 - Oct 6

A hotel room with a bed, a desk, a chair, a ceiling fan, and a TV.

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

West Point

￥44,639 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a bed, dresser, and a ceiling fan.

18. 3-bedroom cottage in superb Tupelo with cool AC breeze

Tupelo

"This cottage was the perfect place for my kids and me to stay in Tupelo. We were there during a difficult family situation, and this home truly felt like a safe, comfortable place to land. The owner was incredibly kind, thoughtful, and accommodating, even allowing my aunt to stay with us when she needed a break from the hospice facility. She also left treats and made us feel completely welcome.The house has so much charm and character, with beautiful antiques and a fun little toy cinema that my...

Susan C.

￥48,712 total

includes taxes & fees

Oct 17 - Oct 18

A two-story house with a front porch, a garage, and a well-maintained lawn.

19. Delightful 4-bedroom house with AC in charming Thaxton

Thaxton

￥714,060 total

includes taxes & fees

Oct 2 - Oct 3

20. 2 Full Beds | Smoking, Micfridge

Tupelo

Anonymous traveler

￥10,628 total

includes taxes & fees

Oct 4 - Oct 5

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Top Chickasaw County Hotel Reviews

Comfort Suites North Tupelo

10/10 Excellent

"Clean hotel, safe area, friendly staff, comfortable bed"

Studio 6 Suites Tupelo, MS - North

10/10 Excellent

"The first floor was scary and dark as soon as we stopped there for a break and to rest they gave us a smoking room on the first floor got to the room and the lights wouldn’t turn on in the room at all. Then the man at the front gave us a room on second floor. We found a dirty needle in the room. It was absolutely disgusting."

Holiday Inn Express Hotel & Suites Tupelo by IHG

10/10 Excellent

"The front assistant was very professional checking in and going out! The room was clean., as was the rest of the hotel! We appreciated the great breakfast crew because the morning we stayed there was the perfect amount of options available for everyone. The food was delicious! I want to say Thank you to the front desk professional that handle a slight issue for me on Sunday morning! She was great and sent word on to her Manager Liz who contacted me and resolved the issue promptly! Thank you and we will return again! Location is good and safe for travelers who are not familiar with Tupelo."

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Vacation Apartments in Chickasaw County

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Chickasaw County vacation rentals

1. Where Historic Charm Meets Comfortable Cottage Stays in Mississippi

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

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

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

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

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