Pike County Vacation Packages

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Your Pike County Vacation

With a Pike County vacation package, you can forget about the stress of planning and simply focus on experiencing all this lively destination has on offer. Expect to have a long sightseeing list during your trip to Pike County. One well-known city you'll want to spend some time exploring is Pittsfield. Quit dreaming and get packing, because your Pike County vacation is just a few clicks away with Expedia.

Top Pike County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
River City Casino & Hotel

River City Casino & Hotel

4 out of 5
Price was CA $1,274, price is now CA $996 per person
CA $996
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,529 reviews)
The room was clean and comfortable but the property is very dated and if you don’t like smelling smoke you will not like this hotel. The staff was friendly and the rooms did not smell like smoke just casino area

Reviewed on May 10, 2026

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,834, price is now CA $1,134 per person
CA $1,134
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,627 reviews)
The entire stay was incredible

Reviewed on May 7, 2026

Hermann Grain Bins BNB

Hermann Grain Bins BNB

2 out of 5
Price was CA $3,011, price is now CA $2,171 per person
CA $2,171
per person
Jul 28 - Aug 4
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to St. Louis (STL)
2/10 (1 review)
Osceola

Osceola

2 out of 5
Mount Pleasant
Price was CA $6,050, price is now CA $4,932 per person
CA $4,932
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to St. Louis (STL)
No reviews
The Cheshire

The Cheshire

4 out of 5
Price was CA $1,334, price is now CA $1,097 per person
CA $1,097
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,007 reviews)
The hotel in general is starting to be run down and not clean. Breakfast was cold!

Reviewed on May 11, 2026

Pike County Hotel Deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
The price is CA $109 per night from May 12 to May 13
CA $109
CA $120 total
May 12 - May 13
includes taxes & fees
9.2/10 Wonderful! (355 reviews)
Enjoyable and pleasant surroundings. The quaint hotel is located on the town square with an in-house restaurant and shops and a great pizza parlor close by. Everyone was friendly and helpful.

Reviewed on Apr 29, 2026

William Watson Hotel
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Griggsville IL
9.8/10 Exceptional! (80 reviews)
Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house.

Reviewed on Oct 6, 2025

Get rates
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
The price is CA $79 per night from May 24 to May 25
CA $79
CA $87 total
May 24 - May 25
includes taxes & fees
Rodeway Inn Pittsfield
See all 214 properties in Pike County
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 Pike County vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Pike County from just CA $996. And the more you bundle, the more cash you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Pike County?
Bundle your hotel and flight bookings, add on extras such as tours, and save with a Pike County vacation package. You won't just pick up superb discounts on your adventure — you'll have a world of choice too. When you book with Expedia, you can select from more than 550 air carriers and 1,000,000 properties all over the world. Your dream vacation begins right here, right now!
What are the top hotels in Pike County?
When it comes to hotels in Pittsfield, Green Acres Hotel and Rodeway Inn are two excellent options. If you're also heading to Pleasant Hill, William Watson Hotel and Monroe Street Suites will make you feel right at home.
How far in advance should I book my Pike County vacation?
It can be hard to know exactly when is the ideal time to book your vacation to Pike County. But usually the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels nearly a year before your departure date. If you're eager to escape on a last-minute getaway, no need to fret! There are incredible deals popping up on Expedia all the time.
What does an Expedia Pike County travel package include?
From airfares and hotels to car rentals, Expedia can help you craft a Pike County package that's right for you. Vacationing for a week or longer? Consider a hotel, flight and rental car bundle. If your break is short, a hotel and airfare deal could be what you're after. Experiences can also be added after you've booked. Our travel packages make it a cinch to save and plan.
What should I know before booking a Pike County travel package?
A travel package can be easier on the credit card than individually booking everything you need for your escape. For example, combine your hotels, flights and rental cars and save a tidy sum. Whatever your vacation goals are, you're bound to find a package within your budget.
Can I choose my airline with a Pike County Expedia vacation package?
Most definitely. Expedia has more than 550 airline partners to choose from globally. With such a big range of choice, finding the perfect carrier to fly you to Pike County will be a cinch.
If I'm not able to travel, can I cancel my Pike County vacation package?
Your situation can change suddenly, so yes. You may be able to cancel or amend your Pike County vacation package for free if you've booked in the last 24 hours. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Want more information? Take a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.