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Chickasaw County Vacation Rentals

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Top cities in Chickasaw County

Vacation Rentals

Houston

Houston

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chickasaw County vacation rentals

A modern kitchen with a central island, bar stools, white cabinetry, and a stainless steel refrigerator.

1. Where Historic Charm Meets Comfortable Cottage Stays in Mississippi

Where Historic Charm Meets Comfortable Cottage Stays in Mississippi
Houston
The price is CA $569
CA $910 total
includes taxes & fees
Nov 16 - Nov 17
Where Historic Charm Meets Comfortable Cottage Stays in Mississippi
A two-story house with a front porch, a small tree, and a brick foundation.

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 CA $569
CA $910 total
includes taxes & fees
Nov 23 - Nov 24
Where Historic Charm Meets Comfortable Cottage Stays at The Oak in Mississippi
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

Cozy 1-bedroom house in charming West Point with AC, WiFi
West Point
9.6 out of 10, Exceptional, (27 reviews)
"Great property for a short stay."
United States
Ronnie R.
The price is CA $100
CA $141 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom house in charming West Point with AC, WiFi
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

Relax to the hum of alpacas just off the balcony of this former Amish store
Pontotoc
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $181
CA $292 total
includes taxes & fees
Nov 16 - Nov 17
Relax to the hum of alpacas just off the balcony of this former Amish store
A wooden deck with a railing, overlooking a forested area and a body of water.

5. 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, (63 reviews)
"Comfortable cabin and beautiful surroundings!"
United States
Gary
The price is CA $212
CA $387 total
includes taxes & fees
Nov 17 - Nov 18
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
A modern kitchen with a large island, stainless steel appliances, and a dining area with wooden chairs.

6. Highland House | 3BR Near Oxford/Tupelo + Patio

Highland House | 3BR Near Oxford/Tupelo + Patio
Pontotoc
The price is CA $190
CA $411 total
includes taxes & fees
Nov 23 - Nov 24
Highland House | 3BR Near Oxford/Tupelo + Patio
A dining area with a wooden table and chairs, a blue armchair, and a painting on the wall.

7. 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, (2 reviews)
"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 CA $281
CA $435 total
includes taxes & fees
Nov 19 - Nov 20
Downtown Loft Cozy 1-bedroom apartment in adorable Aberdeen with WiFi
A cabin-style building with a central open area, surrounded by a forest.

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)
"Perfect place! "
United States
April F.
The price is CA $331
CA $362 total
includes taxes & fees
Nov 17 - Nov 18
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
A cabin-style building with a central open area, surrounded by a forest.

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, (10 reviews)
"this was the cutest property and the hot tub was amazing after a long drive. The tiny home feels spacious and is cozy and comfortable. We loved it and would stay here again!"
United States
jen s.
The price is CA $331
CA $362 total
includes taxes & fees
Nov 17 - Nov 18
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
A hotel room with a bed, a desk, a chair, a ceiling fan, and a TV.

10. 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 CA $243
CA $372 total
includes taxes & fees
Nov 17 - Nov 18
The Duplex - 2 bedroom/1 bath, full kitchen duplex unit - family & pet friendly.
A modern kitchen with a central island, stainless steel appliances, and a bar area with stools.

11. 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 CA $255
CA $542 total
includes taxes & fees
Nov 17 - Nov 18
Pink House Social
A hotel entrance with a covered walkway, a bench, and a parking area.

12. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Tupelo
10.0 out of 10, Exceptional, (163 reviews)
"Needed an overnight stop. Room was well organized and met my needs perfectly."
United States
Anonymous traveller
The price is CA $79
CA $86 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Non-Smoking, Micfridge
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

Modern Historic Family Retreat House in Downtown Tupelo
Tupelo
10.0 out of 10, Exceptional, (6 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 CA $264
CA $549 total
includes taxes & fees
Nov 29 - Nov 30
Modern Historic Family Retreat House in Downtown Tupelo
A living room with a brown leather sofa, a green armchair, a wooden coffee table, and a cowhide rug.

14. The Sugar Shack Cottage with Hot Tub

The Sugar Shack Cottage with Hot Tub
Tupelo
9.8 out of 10, Exceptional, (52 reviews)
"Nice clean place to stay in a convenient area"
United States
Evan D.
The price is CA $213
CA $473 total
includes taxes & fees
Dec 6 - Dec 7
The Sugar Shack Cottage with Hot Tub
A modern kitchen with a marble countertop, stainless steel appliances, and wooden flooring.

15. Bristow Bungalow

Bristow Bungalow
Tupelo
9.0 out of 10, Wonderful, (44 reviews)
"Host was helpful and the house was clean!"
United States
Eugene F.
The price is CA $212
CA $380 total
includes taxes & fees
Nov 16 - Nov 17
Bristow Bungalow
Living area

16. Hollywood Bungalow

Hollywood Bungalow
Tupelo
10.0 out of 10, Exceptional, (39 reviews)
"This is a must a little slice if hippy heaven haven!!"
United States
Jaşmíné B.
The price is CA $207
CA $523 total
includes taxes & fees
Nov 15 - Nov 16
Hollywood Bungalow
A kitchen with white cabinets, stainless steel appliances, a wooden island with chairs, and a ceiling light fixture.

17. The Callaway Cottage- HOME AWAY FROM HOME!

The Callaway Cottage- HOME AWAY FROM HOME!
Tupelo
9.2 out of 10, Wonderful, (31 reviews)
"BEAUTIFUL HOME!!! LOVE LOVE LOVE the fire pit outside"
United States
Tamya A.
The price is CA $186
CA $350 total
includes taxes & fees
Nov 16 - Nov 17
The Callaway Cottage- HOME AWAY FROM HOME!
A spacious kitchen with a wooden ceiling, a large island, and modern appliances.

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

Delightful 4-bedroom house with AC in charming Thaxton
Thaxton
The price is CA $5,135
CA $6,179 total
includes taxes & fees
Nov 15 - Nov 16
Delightful 4-bedroom house with AC in charming Thaxton
A hotel entrance with a covered walkway, a bench, and a parking area.

19. 1 King Bed | Suite, Non-Smoking, Sofa-Bed

1 King Bed | Suite, Non-Smoking, Sofa-Bed
Tupelo
10.0 out of 10, Exceptional, (147 reviews)
"Solid balance between pricing and quality stays compared to other motels I've recently visited."
United States
Anonymous traveller
The price is CA $112
CA $123 total
includes taxes & fees
Nov 15 - Nov 16
1 King Bed | Suite, Non-Smoking, Sofa-Bed
A hotel entrance with a covered walkway, a bench, and a parking area.

20. 2 Full Beds | Smoking, Micfridge

2 Full Beds | Smoking, Micfridge
Tupelo
10.0 out of 10, Exceptional, (146 reviews)
"Good atmosphere by the poolside area made relaxing enjoyable after our long drive!"
United States
Anonymous traveller
The price is CA $79
CA $86 total
includes taxes & fees
Nov 23 - Nov 24
2 Full Beds | 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

A Holiday Inn Express & Suites building with a prominent entrance, columns, and a clear sky.
Holiday Inn Express Hotel & Suites Tupelo by IHG

Holiday Inn Express Hotel & Suites Tupelo by IHG

Holiday Inn Express Hotel & Suites Tupelo by IHG
Tupelo

10/10 Excellent

Daneil was so very kind and helpful! The beds are amazing! Definitely would stay here again!
Canada
Glenda
Reviewed February 27, 2025
Holiday Inn Express Hotel & Suites Tupelo by IHG

Find out more about Chickasaw County

Everything you need to know about Chickasaw County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chickasaw County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chickasaw County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chickasaw County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chickasaw County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chickasaw County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chickasaw County vacation rentals we have selected for you start as low as CA $78 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chickasaw County rentals

At Expedia, we put the best Chickasaw County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chickasaw County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chickasaw County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chickasaw County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.