Pittsfield, IL

Travel Guide

A historic building with a prominent tower and an American flag.
A historic building with a prominent tower and an American flag.
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
$71 nightly
The price is $78 total per night from Oct 15 to Oct 16
$78 total
Oct 15 - Oct 16
Total with taxes and fees
Stay at this hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County ...
9.2/10 Wonderful! (378 reviews)
"Everything was excellent. Very nice and friendly and helpful"

Reviewed on Oct 5, 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
$59 nightly
The price is $64 total per night from Nov 1 to Nov 2
$64 total
Nov 1 - Nov 2
Total with taxes and fees
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid House are located ...
6.8/10 (143 reviews)
"Let’s see…door wouldn’t lock, key card didn’t work right, AND to top it all off, NO HOT WATER!!!i …asked for a refund"

Reviewed on Sep 27, 2026

Rodeway Inn Pittsfield
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St Pittsfield IL
$94 nightly
The price is $103 total per night from Oct 14 to Oct 15
$103 total
Oct 14 - Oct 15
Total with taxes and fees
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions John Greene Shastid House and Pike County Historic ...
9.8/10 Exceptional! (71 reviews)
"Best place Ive stayed period. 100 percent recommend"

Reviewed on Sep 30, 2026

Monroe Street Suites
See all 69 properties in Pittsfield
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.
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

Griggsville IL
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Old Orchard Country ...
10/10 Exceptional! (84 reviews)
"This is an expensive property and home, very well maintained, easily able to accommodate a large family group. The large inground pool with slide and a diving platform was fantastic. The young children in our group spent the majority of their time in the pool! The adults enjoyed the pool just as ..."

Reviewed on Aug 13, 2026

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns

Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns

Pike County IL
Stay at this vacation home in Pittsfield. Enjoy free WiFi, a water park, and a garden. Popular attractions King Park and John Greene Shastid House are located ...
Family-Friendly Lakefront Cabin | Water Fun, Fire Rings & Open Lawns
Family-Friendly Lake Cabin | Pool Access & Scenic Outdoor Grounds

Family-Friendly Lake Cabin | Pool Access & Scenic Outdoor Grounds

Pike County IL
Stay at this cabin in Pittsfield. Enjoy free WiFi, a water park, and a garden. Popular attractions King Park and John Greene Shastid House are located ...
Family-Friendly Lake Cabin | Pool Access & Scenic Outdoor Grounds
See all properties in Pittsfield
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.

Stay near popular Pittsfield 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

Frequently asked questions

Is Pittsfield worth visiting?
Pittsfield is worth visiting for travelers seeking local attractions like King Park and the Old Orchard Country Club. The destination also offers a diverse food scene, with cuisine types including Italian and North American options.
When is the best time to visit Pittsfield?
The best time to visit Pittsfield is from May through September, when the climate is typically mild and pleasant for exploring. For fewer crowds and better value, the quieter months of November through February are a good option, offering a chance to experience the area's winter beauty with cooler temperatures.
What is Pittsfield known for?
Pittsfield is known for its cultural heritage, highlighted by the Pike County Historic Museum. Travelers can also enjoy outdoor recreation at King Park and golf at Old Orchard Country Club. The city offers a strong Italian food culture for visitors to experience.
What is a good itinerary length for Pittsfield?
A good itinerary length for Pittsfield is one to two days to explore highlights like King Park and the Pike County Historic Museum. For a more relaxed trip, or to enjoy activities such as the Old Orchard Country Club, consider a three to four-day stay. This allows travelers to experience the area at a comfortable pace.
What are the top things to do in and around Pittsfield?
Pittsfield offers historical landmarks and natural spaces for travelers to explore:


How do I plan a trip to Pittsfield?
To plan your trip to Pittsfield, search for places to stay on Expedia and book your flights and rental car in advance. Consider activities like visiting King Park, Old Orchard Country Club, or the Pike County Historic Museum. Remember to pair outdoor plans with indoor backups for weather flexibility, ensuring a smooth trip.
What cuisines can you find in Pittsfield?
In Pittsfield you can find New American cuisine, featuring dishes like gourmet burgers, artisanal pizzas, and updated comfort food. Travelers can also enjoy options from Italian, Mexican, and Chinese cuisines. The area also offers a variety of coffee shops and pubs.
Can I book a refundable hotel in Pittsfield?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Pittsfield by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Pittsfield with Expedia?
Expedia makes it easier to plan your Pittsfield trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Pittsfield?
The best choice depends on your travel style. Hotels in Pittsfield can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Pittsfield trip on Expedia?
Once you've booked your Pittsfield trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Pittsfield trip?
Expedia offers customer support before, during, and after your Pittsfield trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Pittsfield?
If it's your first trip to Pittsfield, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Pittsfield hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Pittsfield hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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