Gillespie Vacations from $314

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Your Gillespie Vacation

With a vacation package to Gillespie, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before departing, so you can enjoy each moment discovering this exciting city. Your trip to Gillespie wouldn't be complete without exploring its top attractions, like Piney Creek Ravine - State Natural Area. Whoever you're going away with and whether your budget is big or small, your dream Gillespie vacation is just a few clicks away with Expedia.

The Latest Gillespie vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites St. Louis West - Fenton by IHG

Holiday Inn Express & Suites St. Louis West - Fenton by IHG

3 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 27
found 3 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
8.8/10 Excellent! (1,000 reviews)
great hotel clean and staff was fantasic

Reviewed on Aug 3, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to St. Louis (STL)
9.2/10 Wonderful! (1,550 reviews)
The bed was horrific. The amount of mildew on the shower head was pretty crazy as well. To take a good shower, you'd have to be about 5 foot 5 inches with how low the shower head hung

Reviewed on Aug 6, 2025

The Principal Hotel

The Principal Hotel

3.5 out of 5
Save 100% on your flight
per person
Oct 23 - Oct 27
found 3 hours ago
Roundtrip flight included
New York (NYC) to St. Louis (STL)
9.8/10 Exceptional! (105 reviews)
Very pleasant, super clean… Definitely recommend if you’re in the area. St Louise has a lot to offer, best part was Cahokia pyramids (wish they were renovated relating to past versions) and of course a teip to the top of Gateway Arch.

Reviewed on Aug 6, 2025

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Austin (AUS) to St. Louis (STL)
8.6/10 Excellent! (114 reviews)
It was very clean and nicely decorated. The house is a cool old building. The AC worked great (important, as it was super muggy outside.) I was only there for a couple nights but I think it would have worked well for a longer stay.

Reviewed on Jul 9, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to St. Louis (STL)
8.2/10 Very Good! (758 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on Jul 26, 2025

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Gillespie Hotel Deals

Baymont by Wyndham Litchfield

Baymont by Wyndham Litchfield

2.5 out of 5
1405 W Hudson Dr, Litchfield, IL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Aug 10 to Aug 11
$98 total
Aug 10 - Aug 11
Total includes taxes and fees
8.2/10 Very Good! (1,004 reviews)
"Excellent experience"

Reviewed on Aug 3, 2025

Baymont by Wyndham Litchfield
Super 8 by Wyndham Staunton

Super 8 by Wyndham Staunton

2 out of 5
1527 Herman Rd, Staunton, IL
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $75 total per night from Aug 10 to Aug 11
$75 total
Aug 10 - Aug 11
Total includes taxes and fees
8.4/10 Very Good! (735 reviews)
"Receptionist was incredibly helpful, since I accidentally booked the wrong day."

Reviewed on Aug 4, 2025

Super 8 by Wyndham Staunton
Holiday Inn Express & Suites Litchfield West by IHG

Holiday Inn Express & Suites Litchfield West by IHG

2.5 out of 5
4 Thunderbird Circle, Litchfield, IL
Fully refundable
$121 nightly
The price is $133 total per night from Sep 5 to Sep 6
$133 total
Sep 5 - Sep 6
Total includes taxes and fees
9.4/10 Exceptional! (545 reviews)
"Hotel, ourroom, pool and gym was updated and cleaned"

Reviewed on Jul 29, 2025

Holiday Inn Express & Suites Litchfield West by IHG
See all 32 properties in Gillespie
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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Frequently asked questions

How much does a Gillespie vacation package cost?
Offering great value package deals from $314 on Expedia, you'll be pleasantly surprised at how much a vacation to Gillespie costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Gillespie?
If you're hoping to book a cheap Gillespie vacation package, consider traveling in December, January and February. You're likely to find lower prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Gillespie?
The ideal duration of your Gillespie vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to visit all the major attractions and explore some hidden gems along the way.
How to find the best Gillespie package deals?
Bagging a cheap Gillespie package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Gillespie package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Gillespie vacation as a package?
You can enjoy significant savings on your next Gillespie retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel 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 Gillespie?
If you have your Gillespie travel dates locked in, book as early as you can to snap up some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Gillespie vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Gillespie trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.