Gillespie Vacations from $572
Book a Hotel + Flight or Car together to unlock savings
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
- Crowne Plaza St. Louis Airport by IHG
Dec 23 - Dec 28Crowne Plaza St. Louis Airport by IHG + Flight
Bridgeton5 nights3.5 star property8.0/10 - Very good (1,000 reviews)Roundtrip • Dallas (DAL) - St. Louis (STL)DAL - STL • Nonstop STL - DAL • Nonstop$700$572found 0 hours agoper traveler - The Wildwood Hotel
Dec 23 - Dec 28The Wildwood Hotel + Flight
Wildwood5 nights3.5 star property9.2/10 - Wonderful (1,682 reviews)"Everything was good. Seemed that the property was not full but we were forced into a suite."Reviewed November 7, 2026Roundtrip • Dallas (DAL) - St. Louis (STL)DAL - STL • Nonstop STL - DAL • Nonstop$1,105$657found 0 hours agoper traveler - Remodeled and Inviting Free EV
Jan 28 - Jan 31Remodeled and Inviting Free EV + Flight
Fenton3 nights2.0 star property9.4/10 - Exceptional (3 reviews)"We had a great time with my family ❤️ thank you"Reviewed October 12, 2026Roundtrip • New York (EWR) - St. Louis (STL)EWR - STL • Nonstop STL - EWR • Nonstop$922$678found 1 hour agoper traveler - The Cheshire
Dec 23 - Dec 28The Cheshire + Flight
Richmond Heights5 nights4.0 star property8.8/10 - Excellent (1,004 reviews)"Room was dirty as well as the property"Reviewed November 7, 2026Roundtrip • Dallas (DAL) - St. Louis (STL)DAL - STL • Nonstop STL - DAL • Nonstop$1,008$798found 0 hours agoper traveler - Landing Furnished Apartments near Gateway Arch
Dec 30 - Jan 2Landing Furnished Apartments near Gateway Arch + Flight
Downtown West3 nights3.0 star propertyRoundtrip • Los Angeles (LAX) - St. Louis (STL)LAX - STL • Nonstop STL - LAX • 1 stop$1,050$856found 1 day agoper traveler
Where to stay near Gillespie
Litchfield
For travelers seeking a memorable trip, Litchfield offers a delightful blend of outdoor adventures and cultural experiences. With attractions like the Litchfield Museum and Route 66 Welcome Center, the historic City Hall, and the serene Madison Park, visitors can immerse themselves in the local charm. Located about 12 miles by car from Gillespie, Litchfield serves as a convenient base for exploring the area while enjoying a welcoming atmosphere. Booking a stay here ensures easy access to recreation and scenic beauty.
East Gillespie
Experience the charm of East Gillespie, an excellent hub for family and nature-loving travelers who want to explore attractions like Lake Ka-Ho for outdoor fun, the Litchfield Museum and Route 66 Welcome Center for a taste of local history, and the picturesque Carlinville Public Square. With its welcoming atmosphere and year-round appeal, East Gillespie is about 0.9 mile from Gillespie, making it a smart choice for your next getaway.
Mount Clare
If you are a family traveler or a nature enthusiast, look no further than Mount Clare, which features a vibrant blend of outdoor activities and urban experiences. With attractions like the picturesque Lake Ka-Ho and the historical Litchfield Museum and Route 66 Welcome Center, there’s something for everyone. Just about 2 miles from Gillespie, Mount Clare offers easy access to its urban park and Beaver Dam State Park, making it an ideal choice for your vacation stay. Enjoy the charm of this welcoming city while exploring its many delights.
Eagarville
Immerse yourself in Eagarville, where family-focused travelers can easily access the natural beauty of Lake Ka-Ho and the rich history showcased at the Litchfield Museum and Route 66 Welcome Center. This charming city offers a budget-friendly stay with attractions like the historic Litchfield City Hall to explore. Located about 2 miles from Gillespie, Eagarville is a smart choice for your next vacation, providing a welcoming atmosphere for a memorable getaway.
Benld
Travelers visiting the area will find Benld to be the ideal base for their vacation, featuring a charming mix of family-friendly activities and beautiful natural scenery. With attractions like Lake Ka-Ho for outdoor fun, the Litchfield Museum and Route 66 Welcome Center for history buffs, and the local sports facility stadium for entertainment, there's something for everyone. Located about 3 miles from Gillespie, Benld offers a welcoming atmosphere that makes it a smart choice for your stay.
Gillespie Hotel Deals
Holiday Inn Express & Suites Litchfield West by IHG
Holiday Inn Express & Suites Litchfield West by IHG"clean room, good breakfast"
Hampton Inn by Hilton Litchfield
Hampton Inn by Hilton Litchfield
Quality Inn Litchfield Route 66
Quality Inn Litchfield Route 66"Rooms need updating"
Americas Best Value Inn Litchfield
Americas Best Value Inn Litchfield"BUGS! BUGS! BUGS! DON'T STAY HERE!"
Frequently Asked Questions
How much does a Gillespie vacation package cost?
Offering great value package deals from $572 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.