Vacation Rentals in Chickasaw County

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Top Vacation Rentals in Chickasaw County

Our top choices for Chickasaw County vacation rentals

The Sugar Shack Cottage with Hot Tub
Exterior

The Sugar Shack Cottage with Hot Tub

10.0 out of 10, Exceptional, (26)
"Loved the decor! It was such a comfortable stay. I really enjoyed the home!"
The price is ￥23,378
￥50,934 total
includes taxes & fees
Sep 14 - Sep 15
The Sugar Shack Cottage with Hot Tub
Southern Charm and Convenience: Perfect VRBO Retreat Near Ole Miss and Tupelo.
Dining

Southern Charm and Convenience: Perfect VRBO Retreat Near Ole Miss and Tupelo.

9.6 out of 10, Exceptional, (7)
"We had a great visit. Dee and her husband went above and beyond to make us welcome. My son enjoyed the basketball hoop in their backyard. I would highly recommend this place. Only bad experience was it rained 90% of our stay."
Southern Charm and Convenience: Perfect VRBO Retreat Near Ole Miss and Tupelo.
Spacious Historic Downtown home that sleeps up to 10!
Exterior

Spacious Historic Downtown home that sleeps up to 10!

10.0 out of 10, Exceptional, (54)
"Great stay on the way to the beach"
The price is ￥26,333
￥49,689 total
includes taxes & fees
Sep 4 - Sep 5
Spacious Historic Downtown home that sleeps up to 10!
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (6)
"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."
The price is ￥27,171
￥41,680 total
includes taxes & fees
Aug 31 - Sep 1
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
2 minutes from Elvis's Birthplace 5 miles from downtown Tupelo MS.
Exterior

2 minutes from Elvis's Birthplace 5 miles from downtown Tupelo MS.

9.2 out of 10, Wonderful, (29)
"Good location and very comfortable beds! Will use this VRBO next time I’m in Tupelo "
2 minutes from Elvis's Birthplace 5 miles from downtown Tupelo MS.
Bristow Bungalow
Outdoor dining

Bristow Bungalow

9.8 out of 10, Exceptional, (26)
"Super clean, quiet neighborhood, great location. "
The price is ￥22,790
￥41,158 total
includes taxes & fees
Sep 8 - Sep 9
Bristow Bungalow
Hollywood Bungalow
Exterior

Hollywood Bungalow

9.8 out of 10, Exceptional, (15)
"Very nice property with great eclectic furnishings. We loved our stay! We will book again!"
The price is ￥21,040
￥47,797 total
includes taxes & fees
Sep 2 - Sep 3
Hollywood Bungalow
Charming 2-bedroom house with WiFi and AC in beautiful West Point
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi and AC in beautiful West Point

10.0 out of 10, Exceptional, (2)
"Owner is very understanding, very responsive. Home is comfortable and plenty of room. "
Charming 2-bedroom house with WiFi and AC in beautiful West Point
The Callaway Cottage- HOME AWAY FROM HOME!
Smart TV, fireplace

The Callaway Cottage- HOME AWAY FROM HOME!

9.4 out of 10, Exceptional, (18)
"Ideal cottage in the Joyner District. Clean and nice. Lovely host. 10 of 10. "
The price is ￥19,849
￥38,319 total
includes taxes & fees
Sep 4 - Sep 5
The Callaway Cottage- HOME AWAY FROM HOME!
Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.
Exterior

Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.

10.0 out of 10, Exceptional, (6)
"This place was perfect! It was right across the street from a great restaurant and very close to downtown. The place was clean and very lovely!"
Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.
Cozy 1-bedroom house in charming West Point with AC, WiFi
Microwave, oven, stovetop, coffee/tea maker

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

9.4 out of 10, Exceptional, (13)
"Very clean, nicely decorated and very quiet. We really enjoyed our stay and would be happy to come back."
The price is ￥10,322
￥15,764 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 1-bedroom house in charming West Point with AC, WiFi
Relaxing Prairie Home, 29 Mi to Starkville!
House (3 Bedrooms) | Interior

Relaxing Prairie Home, 29 Mi to Starkville!

3.0 star property
Relaxing Prairie Home, 29 Mi to Starkville!
Quaint cabin style house, modern finish, Beautiful open concept and pond view
Exterior

Quaint cabin style house, modern finish, Beautiful open concept and pond view

2.0 star property
10.0 out of 10, Exceptional, (3)
"This was a clean cabin surrounded by trees with a great view of a pond. Short 15 minute drive into Oxford on beautiful roads. Felt like I was in Vermont in the fall. Enjoyed waking up to the views every morning. Nice wrap around porch with one section screened in. Check in was easy and the host was very responsive. "
Quaint cabin style house, modern finish, Beautiful open concept and pond view
Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.
Dining

Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.

The price is ￥117,624
￥143,792 total
includes taxes & fees
Sep 27 - Sep 28
Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.
•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9
Fridge, microwave, oven, stovetop

•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9

9.4 out of 10, Exceptional, (8)
"Place was clean and host was responsive"
•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9
Downtown Access | Stylish | Family Space
Fridge, microwave, oven, stovetop

Downtown Access | Stylish | Family Space

10.0 out of 10, Exceptional, (2)
"We loved this house. My son and I stayed here for the weekend while attending a football game. We loved that it was a quiet, peaceful property a bit outside of town but certainly close enough that you could get to town in 10 minutes or less. The house had everything you need; nice, comfortable bedding and furniture, tv's in every room, plenty of towels, and everything you'd need in the kitchen. We also loved the awesome covered porch. We will definitely be back and would recommend this place...
Downtown Access | Stylish | Family Space
Charming 2-bedroom house 20 miles from stadium
Interior

Charming 2-bedroom house 20 miles from stadium

The price is ￥51,461
￥75,043 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom house 20 miles from stadium
Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b
2 bedrooms, WiFi, bed sheets

Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b

Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b
Victorian Cottage in Downtown, Small Town, America.
Exterior

Victorian Cottage in Downtown, Small Town, America.

2.0 out of 10, (1)
"I experienced some challenges during my recent stay at the property. Unfortunately, there was an issue with cleanliness, and I noticed some signs of a rat infestation, which made things a bit uncomfortable. The size of the TV was also quite small, about 20 inches, so we didn't get to enjoy any movie nights like we had hoped. Before settling in, I took the initiative to clean the space and ended up spending around $100 on cleaning supplies, including some traps for the rodents. While this...
The price is ￥21,437
￥26,085 total
includes taxes & fees
Sep 8 - Sep 9
Victorian Cottage in Downtown, Small Town, America.
The Heights - Town & Country Living
Exterior detail

The Heights - Town & Country Living

10.0 out of 10, Exceptional, (32)
"Wonderful hosts. They did everything to make our stay comfortable even fresh flowers. They also were great at communicating. The home was very comfortable and plenty of room. "
The Heights - Town & Country Living
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chickasaw County Hotel Reviews

Find out more about Chickasaw County

Find out more about Chickasaw County

Vacation Apartments in Chickasaw County

Search for Vacation rentals in Chickasaw County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Chickasaw County using one of the methods below:

  • View our selection of featured Vacation rentals in Chickasaw County
  • Use the map to find apartments and other Vacation homes in the Chickasaw County neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chickasaw County while they last

Look no further and take a look at our great range of rental properties in Chickasaw County!