Leland Vacations from $685

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Your Leland Vacation

With a Leland vacation package, say goodbye to endless planning and hello to hassle-free adventure. Every detail of your getaway has been taken care of before you depart, so you can get on with discovering this fantastic city. If sightseeing is a must during your trip to Leland, make sure you check out well-known attractions like Highway 61 Blues Museum and Birthplace of Kermit the Frog Museum. Your ultimate Leland vacation is just clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Leland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Room
    Dec 28 - Dec 30

    Americas Best Value Inn Indianola + Flight

    Indianola
    2 nights
    2.5 star property
    7.6/10 - Good (221 reviews)
    "The room was clean and smelled very fresh."
    Reviewed October 18, 2026
    Roundtrip • Columbus (CMH) - Greenville (GLH)
    CMH - GLH • 1 stop GLH - CMH • 1 stop
    $685
    per traveler
    found 16 hours ago
    Americas Best Value Inn Indianola
  • A hotel reception area with a coffee station, a wall with a colorful pattern, and a sofa in the background.
    Dec 27 - Dec 30

    Hampton Inn + Flight

    Indianola
    3 nights
    2.0 star property
    Roundtrip • Columbus (CMH) - Greenville (GLH)
    CMH - GLH • 1 stop GLH - CMH • 1 stop
    $1,055
    $1,041
    per traveler
    found 16 hours ago
    Hampton Inn
  • A hotel dining area with a large granite island, multiple chairs, pendant lighting, a breakfast bar, and a view of the outside.
    Dec 28 - Dec 30

    Holiday Inn Express Hotel & Suites Cleveland by IHG + Flight

    Cleveland
    2 nights
    2.5 star property
    7.8/10 - Good (1,004 reviews)
    "I have a video of roaches in the bathroom on two occasions. I stayed two nights"
    Reviewed November 3, 2026
    Roundtrip • Columbus (CMH) - Greenville (GLH)
    CMH - GLH • 1 stop GLH - CMH • 1 stop
    $747
    $744
    per traveler
    found 16 hours ago
    Holiday Inn Express Hotel & Suites Cleveland by IHG
  • A bedroom with a bed, a nightstand, a dresser, and a wall-mounted TV.
    Dec 27 - Dec 30

    Motel 6 Cleveland, MS - Delta State University + Flight

    Cleveland
    3 nights
    2.0 star property
    8.2/10 - Very good (342 reviews)
    Roundtrip • Columbus (CMH) - Greenville (GLH)
    CMH - GLH • 1 stop GLH - CMH • 1 stop
    $933
    $930
    per traveler
    found 16 hours ago
    Motel 6 Cleveland, MS - Delta State University
  • A hotel room with a bed, a dresser, a television, and a small refrigerator.
    Dec 27 - Dec 30

    c towninn and suites + Flight

    Cleveland
    3 nights
    2.0 star property
    5.8/10 - (33 reviews)
    Roundtrip • Columbus (CMH) - Greenville (GLH)
    CMH - GLH • 1 stop GLH - CMH • 1 stop
    $902
    $902
    per traveler
    found 16 hours ago
    c towninn and suites

Where to stay in and around Leland

Leland offers a charming blend of romance and outdoor adventures. Explore the scenic beauty in Leland's areas, perfect for family-friendly excursions and recreation. Discover the vibrant atmosphere, making it an ideal destination for both couples and adventurous travelers seeking memorable experiences.
A suspension bridge over a river with a cargo ship in the water.

Greenville

For travelers seeking a diverse and engaging getaway, Greenville offers a rich blend of cultural, outdoor, and recreational experiences. Just 8 miles from Leland, this vibrant city is perfect for those interested in exploring landmarks like the 1927 Flood Museum, enjoying nature at Winterville State Park, or unwinding at local casinos. With a steady flow of visitors year-round, Greenville is an ideal choice for hotel bookings, ensuring you have a memorable stay filled with adventure and relaxation.

Stoneville

Experience the charm of Stoneville, an excellent hub for travelers seeking a weekend getaway or family vacation. This quaint village in Leland offers easy access to attractions like the Birthplace of Kermit the Frog Museum, the Highway 61 Blues Museum, and the Greenville Country Club, making it a delightful spot for both leisure and culture. With a steady stream of visitors year-round, Stoneville is a smart choice for your stay, providing a unique blend of entertainment and relaxation.

Metcalfe

Make your vacation planning effortless by staying in Metcalfe, a haven for cultural travelers thanks to its rich history and nearby attractions. Explore the fascinating 1927 Flood Museum, discover the archaeological wonders at Winterville State Park, and enjoy a round of golf at the Greenville Country Club. Located about 7 miles from Leland, Metcalfe offers a unique blend of family-friendly activities and budget-conscious options, making it a smart choice for your stay.

A calm river flanked by dense greenery under a cloudy sky.

Indianola

Immerse yourself in Indianola, where travelers interested in culture and family can easily access unique attractions like the Birthplace of Kermit the Frog Museum and the Highway 61 Blues Museum. With its vibrant urban park, Fletcher Park, and a variety of educational and entertainment options, Indianola offers diverse experiences year-round. Located about 14 miles from Leland, it’s a smart choice for a memorable stay, blending cultural richness with modern amenities.

Shaw

Travelers visiting the area often choose Shaw, especially those seeking a blend of business, family, and cultural experiences. This charming city is perfectly situated near attractions like Delta State University, North Yale Park, and the Roberts-LaForge Library, offering a unique mix of education and outdoor scenery. With visitor numbers peaking in March, July, and October, Shaw remains a vibrant destination year-round. Located about 15 miles from Leland, it’s a smart choice for your stay.

Discover the most popular places to visit in Leland

Highway 61 Blues Museum

9.2/10 (17 reviews)
You can spend time exploring the galleries in Highway 61 Blues Museum during your trip to Leland. Find some time to visit the casinos or churches in this family-friendly area.
See properties

Leland Hotel Deals

Room

Hotel 27

Hotel 27
2.0 star property
9.7 mi from Leland
9.0 out of 10, Wonderful, (382 reviews)
"The coffee was weak and cold and there was no milk. That is a metaphor for the property."
$99 nightly
The price is $109
Nov 15 - Nov 16
Total with taxes and fees
Hotel 27
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.
See all properties in Leland

Frequently Asked Questions

How much does a Leland vacation package cost?

Offering excellent value package deals from $685 on Expedia, you'll be pleasantly surprised at how much a vacation to Leland costs! Expedia's packages make travel planning easier and save you more.

What are the cheapest months to go to Leland?

If you're looking to book a cheap Leland vacation package, consider planning a trip in November, December and January. You'll generally find lower prices on accommodations and flights during these quieter months — ideal for a budget-friendly break.

How many days is enough for Leland?

The ideal duration of your Leland vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to visit all the top sights and discover some hidden treasures along the way.

How to find the best Leland package deals?

Landing a cheap Leland package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.

Is it cheaper to book a Leland vacation as a package?

You can enjoy significant savings on your Leland break by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Leland?

If you're considering a spontaneous Leland trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking well in advance.

Does Expedia offer Book Now, Pay Later Leland vacation packages?

Set off on your dream escape to Leland with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stick to your budget and snap up bargains before they disappear.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.