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.
Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was CA $1,507, price is now CA $1,280 per person
CA $1,280
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8/10 Very good! (1,000 reviews)
Everything thing was great. Very clean.

Reviewed on Jun 29, 2026

The Cheshire

The Cheshire

4 out of 5
Price was CA $1,869, price is now CA $1,498 per person
CA $1,498
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.8/10 Excellent! (1,004 reviews)
fun place to stay and a great location

Reviewed on Jun 30, 2026

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was CA $1,813, price is now CA $1,468 per person
CA $1,468
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
9/10 Wonderful! (1,976 reviews)
When we got in late on Wednesday night, our room was not available. Some BS story about not being cleaned. We had to drive around for hours looking for another place to stay and it cost $400 for one night. The rooftop bars were not available due to either rain or heat. The restaurant closed early every day for breakfast and for dinner.

Reviewed on Jun 30, 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was CA $2,045, price is now CA $1,719 per person
CA $1,719
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Such a great place to stay! We had the best time and will be back

Reviewed on Jun 30, 2026

Hilton St. Louis Airport

Hilton St. Louis Airport

3.5 out of 5
Woodson Terrace
Price was CA $1,665, price is now CA $1,436 per person
CA $1,436
per person
Aug 21 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to St. Louis (STL)
7.6/10 Good! (1,002 reviews)
My room and the common areas were all clean. The establishment looks upscale and well taken care of. *However*, reception staff was clearly in a bad mood, took quite a bit on our parts to get them to be congenial. Secondly, no refrigerator or microwave in the room to be able to heat or store food items that we wanted to enjoy later. So, downstairs we went BUT the community microwave was broken! What!? Another lady ended up waiting for over 20 minutes to get help for that. I went and kindly asked the Maitre of the restaurant to please warn up delicious chicken and hot chocolate. He did, with a kind smile. That is the only thing that somewhat redeemed the rest. Except...the worst part... Mr shower did NOT work!!! It was either very cold or volcano hot. I could only wash by switching the water to the tub fill mode and using the ice container to pour water over me.... Why did the more expensive hotel fail on so many levels. Super disappointing. Super disappointing.

Reviewed on Jun 28, 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 $121 per night from Jul 13 to Jul 14
CA $121
CA $133 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (364 reviews)
"The check-in process was extremely easy. The atmosphere was wonderful, clean rooms, we loved everything about the hotel!"

Reviewed on Jun 21, 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
The price is CA $86 per night from Jul 21 to Jul 22
CA $86
CA $94 total
Jul 21 - Jul 22
includes taxes & fees
6.8/10 (139 reviews)
"Don’t do it!!!! Trust me. No soap, no ice, hardly AC. Would not get into shower for at all. Terrible"

Reviewed on Jun 18, 2026

Rodeway Inn Pittsfield
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

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PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
See all 213 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 $1,280. 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.

Stay near popular Pike County attractions

Old Orchard Country Club

8.8/10 (8 reviews)
Enjoy a round of golf in Pittsfield at Old Orchard Country Club. Experience the area's entertainment venues and theater scene.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.