Sherman Vacations from $316

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The Latest Sherman vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Desoto

Best Western Plus Desoto

2.5 out of 5
Price was $339, price is now $316 per person
$316
per person
Aug 20 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Tupelo (TUP)
8.4/10 Very Good! (929 reviews)
O

Reviewed on Jun 30, 2026

Candlewood Suites Olive Branch by IHG

Candlewood Suites Olive Branch by IHG

2.5 out of 5
Price was $561, price is now $489 per person
$489
per person
Aug 12 - Aug 19
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Tupelo (TUP)
8/10 Very Good! (198 reviews)
Amazing staff and room. I was surprised for my room to be a nice as it was for the price. Everyone was super helpful and understanding when I had an extra guest.

Reviewed on Jun 17, 2026

Holiday Inn Express & Suites Olive Branch by IHG

Holiday Inn Express & Suites Olive Branch by IHG

2.5 out of 5
Price was $346, price is now $321 per person
$321
per person
Aug 20 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Tupelo (TUP)
8.6/10 Excellent! (1,005 reviews)

La Quinta Inn & Suites by Wyndham Olive Branch

La Quinta Inn & Suites by Wyndham Olive Branch

2.5 out of 5
Price was $353, price is now $335 per person
$335
per person
Aug 20 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Tupelo (TUP)
9.4/10 Exceptional! (326 reviews)
Second time staying here and it was great again! Did not disappoint.

Reviewed on Jun 29, 2026

Historic Whispering Woods Hotel & Conference Center

Historic Whispering Woods Hotel & Conference Center

3 out of 5
Price was $339, price is now $322 per person
$322
per person
Aug 20 - Aug 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Tupelo (TUP)
7.4/10 Good! (1,002 reviews)
A little underwhelming. The room were janky. The pool was pretty nice.

Reviewed on Jul 2, 2026

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Sherman Hotel Deals

Best Western Plus Tupelo Inn & Suites

Best Western Plus Tupelo Inn & Suites

2.5 out of 5
3158 N Gloster Street Tupelo MS
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $104 total per night from Jul 5 to Jul 6
$104 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Great overnight stop. Clean and affordable. Friendly staff."

Reviewed on Jul 3, 2026

Best Western Plus Tupelo Inn & Suites
Baymont by Wyndham Tupelo

Baymont by Wyndham Tupelo

2.5 out of 5
625 Spicer Drive Tupelo MS
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $72 total per night from Jul 26 to Jul 27
$72 total
Jul 26 - Jul 27
Total with taxes and fees
7.6/10 Good! (1,002 reviews)
"Everything was good. Will stay here again"

Reviewed on Jul 2, 2026

Baymont by Wyndham Tupelo
Red Roof Inn Tupelo

Red Roof Inn Tupelo

2 out of 5
1516 Mccullough Blvd Tupelo MS
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $71 total per night from Jul 9 to Jul 10
$71 total
Jul 9 - Jul 10
Total with taxes and fees
8.2/10 Very Good! (1,015 reviews)
"Has everything you need.Clean and helful friendly staff.Room was perfect.Impressed"

Reviewed on Jul 1, 2026

Red Roof Inn Tupelo
See all 130 properties in Sherman
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.

Find the Best Sherman Vacation Packages

Sherman Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tupelo Regional Airport (TUP)
Population
680

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Frequently asked questions

How much does a Sherman vacation package cost?
You can snap up a vacation package to this destination from $316 on Expedia. However, how much your vacation to Sherman costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Sherman?
You can usually find lower rates and greater availability in February, June and July. Take a look at our cheap Sherman vacation packages and you could land some excellent off-season deals.
How many days is enough for Sherman?
Typically, a handful of days is enough to check out the major attractions during your Sherman vacation. However, if you prefer to have more time to chill out or take day trips, think about extending your trip.
How to find the best Sherman package deals?
Use Expedia's filter tool to find some fabulous Sherman package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Sherman package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Sherman vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Sherman vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Sherman?
Score amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Sherman escape.
Does Expedia offer Book Now, Pay Later Sherman vacation packages?
Your Sherman break is meant to be an escape from your daily routine, not a reason for money worries. So to give you extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.