Pleasant Hill Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Pleasant Hill Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Residence Inn by Marriott St Louis Downtown

Residence Inn by Marriott St Louis Downtown

3 out of 5
Midtown
Price was CA $1,628, price is now CA $1,366 per person
CA $1,366
per person
Dec 16 - Dec 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
7.8/10 Good! (1,001 reviews)

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $2,200, price is now CA $1,395 per person
CA $1,395
per person
Dec 16 - Dec 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was CA $2,103, price is now CA $1,692 per person
CA $1,692
per person
Dec 16 - Dec 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)
A wonderful break from boring hotels! My kids loved all the artwork and the scavenger hunt. The pub food and drinks were fantastic, as was the hotel breakfast each morning. We will definitely plan to return.

Reviewed on Nov 9, 2026

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $2,091, price is now CA $1,735 per person
CA $1,735
per person
Dec 16 - Dec 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
9/10 Wonderful! (2,047 reviews)

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $2,151, price is now CA $1,809 per person
CA $1,809
per person
Dec 16 - Dec 23
found 17 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
8.6/10 Excellent! (1,080 reviews)
We were here for a wedding. Our room was very nice but my son’s bathroom was disgusting and not clean, they had to switch rooms and the only compensation they gave them was a food voucher. Not acceptable with blood and vomit not cleaned from previous guest. We expected more for this caliber of hotel.

Reviewed on Nov 8, 2026

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Pleasant Hill Hotel Deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
The price is CA $120 per night from Nov 10 to Nov 11
CA $120
CA $132 total
Nov 10 - Nov 11
includes taxes & fees
9.4/10 Exceptional! (383 reviews)
"Great place"

Reviewed on Nov 2, 2026

William Watson Hotel
River's Edge Motel

River's Edge Motel

2 out of 5
201 Mansion St Louisiana MO
The price is CA $117 per night from Dec 8 to Dec 9
CA $117
CA $133 total
Dec 8 - Dec 9
includes taxes & fees
8.8/10 Excellent! (395 reviews)
"Nice location."

Reviewed on Oct 28, 2026

River's Edge Motel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
The price is CA $97 per night from Nov 30 to Dec 1
CA $97
CA $107 total
Nov 30 - Dec 1
includes taxes & fees
6.8/10 (145 reviews)
"It seems to be still under some remodeling in the room, but was clean... Even tho the bathroom window was frosted glass it still needs a blind.. I kept the light off."

Reviewed on Oct 21, 2026

Rodeway Inn Pittsfield
See all 70 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.
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Frequently asked questions

How much does a Pleasant Hill vacation package cost?
Offering great value package deals from CA $1,366 on Expedia, you'll be thrilled with how little a vacation to Pleasant Hill costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Pleasant Hill?
If you're looking to book a cheap Pleasant Hill vacation package, consider planning a trip in January, February and March. You'll generally find lower prices on flights and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Pleasant Hill?
With a well-organized travel plan, you can easily visit the most popular Pleasant Hill sights in a few days. But if you prefer to discover hidden spots or go on day trips, think about booking your Pleasant Hill vacation for longer.
How to find the best Pleasant Hill package deals?
Start your search for a Pleasant Hill package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Pleasant Hill package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pleasant Hill getaway off to a flying start.
Is it cheaper to book a Pleasant Hill vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Pleasant Hill vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Pleasant Hill?
If you have your Pleasant Hill travel dates finalized, book early to bag some terrific deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Pleasant Hill?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Pleasant Hill.
  2. Set a budget: Consider costs like flights, meals and transportation when calculating how much to put aside for your trip to Pleasant Hill. Then, choose a hotel that suits your budget, whether that's a low-cost stay or a lavish getaway.
  3. Decide your trip length: Think about how long you'd like to spend exploring Pleasant Hill. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, book the ideal Pleasant Hill vacation package for you.

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