Pleasant Hill Vacations

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Find the Best Pleasant Hill Vacation Packages

Pleasant Hill Hotel Deals

Cozy 3 bedroom family friendly home in pike county IL

Cozy 3 bedroom family friendly home in pike county IL

Pleasant Hill
10/10 Exceptional! (2 reviews)
Drop in for deer hunting
"The house was older as expected in Pleasant Hill. Very quiet neighborhood and ample space. Stayed three nights everything was as expected. Owners were awesome and responsive. We have booked for two more stays in the fall. Everything is close for groceries."

Reviewed on Sep 17, 2024

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Cozy 3 bedroom family friendly home in pike county IL
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is ￥11,377 per night from Jul 26 to Jul 27
￥11,377
￥12,512 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (232 reviews)
Definitely would stay here again!
"Really loved the historic of the building. Very clean and comfortable."

Reviewed on Jul 6, 2025

William Watson Hotel
Super 8 by Wyndham Bowling Green

Super 8 by Wyndham Bowling Green

2 out of 5
1216 E Champ Clark Dr, Bowling Green, MO
8.2/10 Very Good! (458 reviews)
"Always stay there for any family functions in Bowling Green"

Reviewed on Jul 20, 2025

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Super 8 by Wyndham Bowling Green
See all 34 properties in Pleasant Hill
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.

Frequently asked questions

How much does a Pleasant Hill vacation package cost?
You'll find cheap prices on Expedia for your Pleasant Hill getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Pleasant Hill costs.
What are the cheapest months to go to Pleasant Hill?
January, February and March are the best times to search for cheap Pleasant Hill vacation packages. Traveling in quieter months means you can typically find lower prices on hotels and flights.
How many days is enough for Pleasant Hill?
Generally, a handful of days is enough to explore the main attractions during your Pleasant Hill vacation. But if you prefer to have some time to rest or take day trips, consider extending your trip.
How to find the best Pleasant Hill package deals?
Bagging a cheap Pleasant Hill package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most affordable Pleasant Hill package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pleasant Hill vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Pleasant Hill vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Pleasant Hill?
Land amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Pleasant Hill break.
How to plan a trip to Pleasant Hill?

  1. Choose the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Pleasant Hill.
  2. Set your budget: Factor in costs such as food, flights and transportation when calculating how much to set aside for your trip to Pleasant Hill. Then, select a hotel that works with your budget, whether that's a low-cost option or a lavish retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Pleasant Hill. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Pleasant Hill vacation package.

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