Chickasaw County Vacations & Trips from $357

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Your Chickasaw County Vacation

Set off on your next epic adventure with a Chickasaw County vacation package, and leave relaxed knowing the finer details are taken care of. Plus with the ability to customize your getaway, it'll be one to remember. You can expect to have a to-do list as long as your arm during your trip to Chickasaw County. One well-known city you'll want to explore is Houston. Expedia has everything you need for organizing your Chickasaw County vacation. From accommodations and flights, to activities and rental cars, we know how to create a travel experience like no other.

Top destinations in Chickasaw County

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

Woodland

Woodland

The Latest Chickasaw County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Historic Whispering Woods Hotel & Conference Center

Historic Whispering Woods Hotel & Conference Center

$357
per person
Nov 18 - Nov 23
found 1 hour ago
Roundtrip flight included
Houston (HOU) to Tupelo (TUP)
7.2/10 Good! (1,001 reviews)
It was a good stay…. Staff could have been a little better but overall it was a nice experience

Reviewed on Aug 29, 2026

Microtel Inn & Suites by Wyndham Olive Branch

Microtel Inn & Suites by Wyndham Olive Branch

$648
per person
Nov 16 - Nov 24
found 1 day ago
Roundtrip flight included
Washington (DCA) to Tupelo (TUP)
9/10 Wonderful! (246 reviews)
Great stay will be back.

Reviewed on Sep 7, 2026

Hotel DeSoto

Hotel DeSoto

$581
per person
Nov 16 - Nov 24
found 1 day ago
Roundtrip flight included
Washington (DCA) to Tupelo (TUP)
8.8/10 Excellent! (1,004 reviews)
Arrived early to check in, the girl at the front stated the person to check me in went to get food! Front lobby smelled of dirty mop water and the floor was sticky. Room was decent but had barely made beds. Loud guests made alot of noise, I checked out a day early at about 4am. The front desk person was sleeping n told me to leave my key at the desk n she limped back to the back to sleep. Called Expedia to refund the night I didn't use and the manager refused to credit me! Dont waste ur time or money booking at this ghetto hotel with terrible customer service

Reviewed on Sep 7, 2026

La Quinta Inn & Suites by Wyndham Olive Branch

La Quinta Inn & Suites by Wyndham Olive Branch

$746
per person
Nov 16 - Nov 24
found 1 day ago
Roundtrip flight included
Washington (DCA) to Tupelo (TUP)
9.4/10 Exceptional! (368 reviews)
Room was so nice and clean. Most definitely will be back if I ever need a hotel.

Reviewed on Sep 7, 2026

Magnolia Inn and Suites Olive Branch

Magnolia Inn and Suites Olive Branch

$566
per person
Nov 16 - Nov 24
found 1 day ago
Roundtrip flight included
Washington (DCA) to Tupelo (TUP)
8.2/10 Very Good! (1,002 reviews)

Find the Best Chickasaw County Vacation Packages

Chickasaw County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Memphis Intl. Airport (MEM)
Top Sights
Davis Lake Recreation Area and Joe Brigance Memorial Park

Chickasaw County Hotel Deals

Holiday Terrace Motel

Holiday Terrace Motel

950 E Madison St Houston MS
Fully refundableReserve now, pay when you stay
$57 nightly
$63 total
Oct 11 - Oct 12
Total with taxes and fees
Holiday Terrace Motel
Best Western Plus Tupelo Inn & Suites

Best Western Plus Tupelo Inn & Suites

3158 N Gloster Street Tupelo MS
Fully refundableReserve now, pay when you stay
$105 nightly
$115 total
Sep 17 - Sep 18
Total with taxes and fees
8.8/10 Excellent! (1,020 reviews)
"Clean room, staff is always nice. Located in a great quiet area and you can walk to several restaurants . Great place to stay."

Reviewed on Sep 10, 2026

Best Western Plus Tupelo Inn & Suites
Baymont by Wyndham Tupelo

Baymont by Wyndham Tupelo

625 Spicer Drive Tupelo MS
Fully refundableReserve now, pay when you stay
$71 nightly
$78 total
Oct 5 - Oct 6
Total with taxes and fees
7.6/10 Good! (1,001 reviews)
"I was there from 9/4 to 9/8 the pool had green water not getting that, the room beds did not get changed until the day before we left, not even made up the beds. We had to request towels 2 times. Staff was apologetic but they need staff. This was my worse stay ever. Oh the smoking yeah people smoked ..."

Reviewed on Sep 9, 2026

Baymont by Wyndham Tupelo
See all 149 properties in Chickasaw County
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.

Stay near popular Chickasaw County attractions

Davis Lake Recreation Area

9.0/10 (2 reviews)
Explore the great outdoors at Davis Lake Recreation Area, a lovely green space in New Houlka.
See properties

Houston Garden Park

9.2/10 (5 reviews)
Explore the great outdoors at Houston Garden Park, a lovely green space in Houston.
See properties

Davis Lake

Commune with nature and explore the great outdoors at Davis Lake during your travels in New Houlka. While you're in the area, wander around the parks.
See properties

Joe Brigance Memorial Park

10.0/10 (1 review)
Explore the great outdoors at Joe Brigance Memorial Park, a lovely green space in Houston.
See properties
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