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Vacation Rentals in Chickasaw County

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Our top choices for Chickasaw County vacation rentals

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

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

2 minutes from Elvis's Birthplace 5 miles from downtown Tupelo MS.
Tupelo
9.4 out of 10, Exceptional, (34)
"Nice clean place to stay. The area was quiet and convenient place to stay so close to Elvis's birthplace."
United States
Eric J.
2 minutes from Elvis's Birthplace 5 miles from downtown Tupelo MS.
Fridge, microwave, oven, stovetop
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 ￥24,101
￥42,525 total
includes taxes & fees
Dec 14 - Dec 15
Bristow Bungalow
Smart TV, DVD player
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, (33)
"We stayed here passing through and it was perfect for our family! "
United States
Leah M.
The price is ￥24,723
￥53,531 total
includes taxes & fees
Dec 14 - Dec 15
The Sugar Shack Cottage with Hot Tub
Exterior
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.
The price is ￥32,497
￥37,155 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cypress - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Smart TV
Charming 2-bedroom cottage in Tupelo with WiFi and AC

Charming 2-bedroom cottage in Tupelo with WiFi and AC

Charming 2-bedroom cottage in Tupelo with WiFi and AC
Tupelo
9.6 out of 10, Exceptional, (4)
"Great stay! Came in town for a wedding and this was the perfect location. Would stay here again!"
United States
Caroline F.
Charming 2-bedroom cottage in Tupelo with WiFi and AC
Dining
Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b

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

Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b
Tupelo
10.0 out of 10, Exceptional, (2)
"Close to amenities!"
United States
Tanya M.
Downtown -All Shook Up Bungalow -Heart Break Hotel 2br/1b
Living area
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 ￥20,851
￥48,712 total
includes taxes & fees
Dec 15 - Dec 16
Hollywood Bungalow
Fridge, microwave, oven, stovetop
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)
"Cute home in nice neighborhood of older homes. Desi responded promptly when we had an issue with the entry code and later with another small issue. The layout of the house was perfect for us. We enjoyed our stay and would stay there again!"
United States
Peggy M.
The price is ￥20,991
￥40,524 total
includes taxes & fees
Dec 14 - Dec 15
The Callaway Cottage- HOME AWAY FROM HOME!
Interior
Heart Break Hotel Rad Bungalow - Rock-n-roll themed 2-bedroom downtown Tupelo.

Heart Break Hotel Rad Bungalow - Rock-n-roll themed 2-bedroom downtown Tupelo.

Heart Break Hotel Rad Bungalow - Rock-n-roll themed 2-bedroom downtown Tupelo.
Tupelo
Heart Break Hotel Rad Bungalow - Rock-n-roll themed 2-bedroom downtown Tupelo.
Interior
Chestnut Cottage - Minutes to Downtown and NMMC! Close to Fairpark & Arena.

Chestnut Cottage - Minutes to Downtown and NMMC! Close to Fairpark & Arena.

Chestnut Cottage - Minutes to Downtown and NMMC! Close to Fairpark & Arena.
Tupelo
9.8 out of 10, Exceptional, (45)
"This cottage was exactly what we were looking for. The location was great, really close to everything we needed."
United States
Curt R.
Chestnut Cottage - Minutes to Downtown and NMMC! Close to Fairpark & Arena.
Terrace/patio
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 ￥23,090
￥44,173 total
includes taxes & fees
Dec 14 - Dec 15
Lakeside luxury cabin on 125 acres. 20 min to MSU - Sleeps 6
House (3 Bedrooms) | Interior
Relaxing Prairie Home, 29 Mi to Starkville!

Relaxing Prairie Home, 29 Mi to Starkville!

Relaxing Prairie Home, 29 Mi to Starkville!
3.0 star property
Prairie
8.0 out of 10, Very Good, (1)
Relaxing Prairie Home, 29 Mi to Starkville!
Interior
Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.

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

Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.
Tupelo
10.0 out of 10, Exceptional, (8)
"This place is amazing and close to everything! This house is full of essentials and very clean! Highly recommend and will be staying when I return to Tupelo! "
United States
Heather B.
Enjoy this elegant artdeco home centrally-located in the heart of Tupelo.
Dining
Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.

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

Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.
Shannon
The price is ￥124,392
￥150,236 total
includes taxes & fees
Dec 13 - Dec 14
Gorgeous 3-bed, 3.5 bath on 32 acres of beautiful farmland, Shannon, MS. WiFi.
House (2 Bedrooms) | Interior
Historic Aberdeen Vacation Home w/ Yard!

Historic Aberdeen Vacation Home w/ Yard!

Historic Aberdeen Vacation Home w/ Yard!
3.0 star property
Aberdeen
Historic Aberdeen Vacation Home w/ Yard!
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
9.8 out of 10, Exceptional, (59)
"So cute and comfortable! We enjoyed it and would stay again!"
United States
Sarah R.
The price is ￥27,848
￥52,548 total
includes taxes & fees
Dec 14 - Dec 15
Spacious Historic Downtown home that sleeps up to 10!
4 bedrooms, desk, iron/ironing board, free WiFi
•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9

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

•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9
Tupelo
9.4 out of 10, Exceptional, (9)
"Cute house in a quiet neighborhood. Very clean. Hosts were very easy to communicate with. "
United States
Mihalis P.
•A Family Haven N' Heart of Tupelo: 4 Bedrooms, 6 Beds, 1.5 Baths Sleeps 8 or 9
Property grounds
Downtown Access | Stylish | Family Space

Downtown Access | Stylish | Family Space

Downtown Access | Stylish | Family Space
Starkville
10.0 out of 10, Exceptional, (2)
"This house is so cozy and comfortable that I honestly didn't want to leave. I love the front porch!! When my husband ,and I relocate here, I want my porch just like it."
United States
Linda T.
Downtown Access | Stylish | Family Space
Exterior
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.
The price is ￥32,497
￥36,656 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cedar - NEW Cottage in woods @ Moon Lake Farm - HOT TUB - LAKE - KAYAK - FISH
Interior
Cozy 1-bedroom house in charming West Point with AC, WiFi

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

Cozy 1-bedroom house in charming West Point with AC, WiFi
West Point
9.4 out of 10, Exceptional, (16)
"Very clean, nicely decorated and very quiet. We really enjoyed our stay and would be happy to come back."
United States
Eugene L.
Cozy 1-bedroom house in charming West Point with AC, WiFi
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

Hampton Inn & Suites Tupelo/Barnes Crossing

Hampton Inn & Suites Tupelo/Barnes Crossing

10/10 Excellent
"Room was clean, spacious nice, probably the only complaint would be the bed not the most comfortable. The staff were amazing, the most helpful I probably encountered in a long time. From the FD, breakfast attendant, to housekeeping.TY it makes a difference. AAnd the Christmas decor was amazing "
Debbie 2-night trip
Posted 13 hours ago
Hampton Inn & Suites Tupelo/Barnes Crossing

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Vacation Apartments in Chickasaw County

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