Holiday Rentals in Chickasaw County

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Featured Holiday Rentals in Chickasaw County

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.

9.8 out of 10, Exceptional, (6)
"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, (52)
"My husband and I enjoyed our stay. The home is well equipped, beds are comfy, and the home was clean!"
The price is €320
includes taxes & fees
16 Sept - 17 Sept
Spacious Historic Downtown home that sleeps up to 10!
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 €129
includes taxes & fees
29 Aug - 30 Aug
Cozy 1-bedroom house in charming West Point with AC, WiFi
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.
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 €171
includes taxes & fees
1 Sept - 2 Sept
Victorian Cottage in Downtown, Small Town, America.
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 €357
includes taxes & fees
16 Sept - 17 Sept
The Sugar Shack Cottage with Hot Tub
The Callaway Cottage- HOME AWAY FROM HOME!
Smart TV, fireplace

The Callaway Cottage- HOME AWAY FROM HOME!

9.4 out of 10, Exceptional, (18)
"Perfect cozy short stay. Would definitely book here again."
The price is €230
includes taxes & fees
16 Sept - 17 Sept
The Callaway Cottage- HOME AWAY FROM HOME!
Bristow Bungalow
Outdoor dining

Bristow Bungalow

10.0 out of 10, Exceptional, (24)
"Super clean, quiet neighborhood, great location. "
The price is €252
includes taxes & fees
16 Sept - 17 Sept
Bristow Bungalow
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Smart TV, books

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

9.8 out of 10, Exceptional, (9)
"Very clean and tucked away."
The price is €246
includes taxes & fees
16 Sept - 17 Sept
Cypress - 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
Microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (5)
"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 €272
includes taxes & fees
16 Sept - 17 Sept
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
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
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 €284
includes taxes & fees
17 Aug - 18 Aug
Hollywood Bungalow
•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
~RomanticRoomForCouple~Gated Condo'NHeartOfTupelo3guests
1 bedroom, desk, iron/ironing board, free WiFi

~RomanticRoomForCouple~Gated Condo'NHeartOfTupelo3guests

9.0 out of 10, Wonderful, (6)
"It was a very convenient and clean stay. John was great with communication and we look forward to coming back soon. "
~RomanticRoomForCouple~Gated Condo'NHeartOfTupelo3guests
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!
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Exterior

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

9.8 out of 10, Exceptional, (45)
"Peaceful waterfront cabin in the woods! Book this place or you’re missing out! "
The price is €248
includes taxes & fees
17 Aug - 18 Aug
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
Cozy Cottage in the country, Pet Friendly. 2.8 mil from Tupelo Furniture Market
Exterior detail

Cozy Cottage in the country, Pet Friendly. 2.8 mil from Tupelo Furniture Market

9.0 out of 10, Wonderful, (2)
"The house was very nice and had everything we needed and our team would love to stay there again next time we are in the are."
Cozy Cottage in the country, Pet Friendly. 2.8 mil from Tupelo Furniture Market
Charming 2-bedroom cottage in Tupelo with WiFi and AC
2 bedrooms, iron/ironing board, WiFi, bed sheets

Charming 2-bedroom cottage in Tupelo with WiFi and AC

9.0 out of 10, Wonderful, (2)
"I had a great experience and amazing stay over the weekend at this property, very great location and the property was beautiful! The host was fantastic and went above and beyond with my accommodations. I highly recommend this house and I will be back in the future! "
Charming 2-bedroom cottage in Tupelo with WiFi and AC
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 €862
includes taxes & fees
14 Sept - 15 Sept
Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.
Historic Aberdeen Vacation Home w/ Yard!
House (2 Bedrooms) | Interior

Historic Aberdeen Vacation Home w/ Yard!

3.0 star property
Historic Aberdeen Vacation Home w/ Yard!
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

La Quinta Inn & Suites by Wyndham Tupelo

La Quinta Inn & Suites by Wyndham Tupelo

10/10 Excellent
"We enjoyed our stay at this hotel. Friendly and courteous staff. We had no problems whatsoever. Will stay here again on our next trip back to Tupelo."
Dorothy 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Tupelo