Pleasant Plains Vacations from $876

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The Latest Pleasant Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Springfield Southeast
Villa DeWolf
Northfield Inn, Suites & Conference Center
Inn at 835 Boutique Hotel
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Pleasant Plains Hotel Deals

Charming barn-turned-home with hot tub & W/D - quiet location & dog-friendly

Charming barn-turned-home with hot tub & W/D - quiet location & dog-friendly

Pleasant Plains
Charming barn-turned-home with hot tub & W/D - quiet location & dog-friendly
Completely remodeled, pet-friendly, 'smart' home in the country!

Completely remodeled, pet-friendly, 'smart' home in the country!

Pleasant Plains
9.8/10 Exceptional! (81 reviews)
"What a wonderful place in the country--and close to Springfield and all its sites. Perfectly peaceful blended with the latest technology. Very responsive owner too. Loved it."

Reviewed on Aug 11, 2025

Completely remodeled, pet-friendly, 'smart' home in the country!
Western Barn

Western Barn

Pleasant Plains
Great location and very quiet.
"As advertised."

Reviewed on Jun 6, 2024

Western Barn
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 Pleasant Plains vacation package cost?
You'll find cheap prices from $876 on Expedia for your Pleasant Plains break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Pleasant Plains costs.
What are the cheapest months to go to Pleasant Plains?
If you'd like to book a cheap Pleasant Plains vacation package, consider traveling in November, December and January. You'll generally find lower rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Pleasant Plains?
Generally, a handful of days is enough to visit the top attractions during your Pleasant Plains vacation. But if you want to have some time to kick back or take day tours, think about extending your itinerary.
How to find the best Pleasant Plains package deals?
Begin your search for a Pleasant Plains package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Pleasant Plains package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasant Plains getaway off to a flying start.
Is it cheaper to book a Pleasant Plains vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Pleasant Plains vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Pleasant Plains?
If you've got your Pleasant Plains vacation dates confirmed, book as early as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Pleasant Plains vacation packages?
Jet off on your perfect escape to Pleasant Plains with help from our Book Now, Pay Later vacations. There's no need to save like crazy or hold off until the next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.