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A city skyline with a prominent arch bridge over a river reflecting city lights.

Overland Vacations from ￥264,660

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  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Overland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Property entrance
    Oct 22 - Oct 27

    The Wildwood Hotel + Flight

    Wildwood
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,670 reviews)
    "Everything was great. Staff was very helpful and friendly. I will definitely stay here next time I am in Missouri."
    Reviewed August 1, 2026
    Roundtrip • Osaka (OSA) - St. Louis (STL)
    KIX - STL • 2 stops STL - KIX • 2 stops
    ￥331,644
    ￥264,660
    per traveler
    found 22 hours ago
    The Wildwood Hotel
  • Gastropub
    Oct 22 - Oct 27

    The Cheshire + Flight

    Richmond Heights
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "Very unique hotel. I love historical feel and whimsy, and this hotel fits both. Very old English feel, with all of the antique looking furniture. Breakfast was included with the room and it was fantastic. The fresh fruit was such a nice treat. You can tell it's not a new hotel, but it was very clean, which is more important to me!"
    Reviewed July 31, 2026
    Roundtrip • Osaka (OSA) - St. Louis (STL)
    KIX - STL • 2 stops STL - KIX • 2 stops
    ￥331,220
    ￥286,283
    per traveler
    found 1 day ago
    The Cheshire
  • Outdoor pool, open 10:00 AM to 6:00 PM, cabanas (surcharge)
    Oct 22 - Oct 27

    Ameristar Casino Resort and Spa + Flight

    St. Charles
    5 nights
    4.5 star property
    8.6/10 - Excellent (1,025 reviews)
    Roundtrip • Osaka (OSA) - St. Louis (STL)
    KIX - STL • 2 stops STL - KIX • 2 stops
    ￥342,386
    ￥300,698
    per traveler
    found 1 day ago
    Ameristar Casino Resort and Spa
  • Indoor pool, open 6:00 AM to 9:00 PM, sun loungers
    Oct 22 - Oct 27

    Crowne Plaza St. Louis Airport by IHG + Flight

    Bridgeton
    5 nights
    3.5 star property
    8.0/10 - Very Good (1,003 reviews)
    Roundtrip • Osaka (OSA) - St. Louis (STL)
    KIX - STL • 2 stops STL - KIX • 2 stops
    ￥325,218
    ￥289,352
    per traveler
    found 1 day ago
    Crowne Plaza St. Louis Airport by IHG
  • Lobby
    Oct 22 - Oct 27

    Hyatt Regency St. Louis at The Arch + Flight

    Downtown St. Louis
    5 nights
    4.0 star property
    8.6/10 - Excellent (4,136 reviews)
    Roundtrip • Osaka (OSA) - St. Louis (STL)
    KIX - STL • 2 stops STL - KIX • 2 stops
    ￥341,467
    ￥307,483
    per traveler
    found 22 hours ago
    Hyatt Regency St. Louis at The Arch

Where to stay in Overland

Find the best Overland areas and neighborhoods for the activities you enjoy most.

Breckenridge Hills

Breckenridge Hills is well-liked for its coffeehouses and sporting events. If you're hoping to see more of the larger area, Westport Plaza and Creve Coeur Golf Club are some interesting sights nearby to check out.

Sycamore Hills

If you're looking for some top things to see and do in Sycamore Hills and surrounding area, you can visit St. Louis Car Museum and Saint Louis Galleria Mall.

Overland Hotel Deals

Lobby

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport
2.5 star property
4.3 km from Overland
9.2 out of 10, Wonderful, (3,116 reviews)
"Very attentive staff. The room was clean and had a mini fridge with a microwave. Safe side of town."
The price is ￥15,424
￥18,160 total
includes taxes & fees
Aug 6 - Aug 7
Pear Tree Inn St. Louis Airport
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 Overland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.