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
$76 nightly
The price is $83 total per night from Oct 23 to Oct 24
$83 total
Oct 23 - Oct 24
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! (375 reviews)
"Very charming, unique hotel. Enjoyed our stay. Be aware if you have trouble with stairs to make sure and book a main level room. Breakfast was very minimal. View of the courthouse and history of building wonderful. Would stay again."

Reviewed on Sep 24, 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
$57 nightly
The price is $63 total per night from Oct 18 to Oct 19
$63 total
Oct 18 - Oct 19
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 ...
Rodeway Inn Pittsfield
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St Pittsfield IL
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $103 total per night from Sep 27 to Sep 28
$103 total
Sep 27 - Sep 28
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 ...
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!
Pine Lakes Outdoor Adventure | Cabin Stay w/ Waterpark Access

Pine Lakes Outdoor Adventure | Cabin Stay w/ Waterpark Access

Pike County IL
Stay at this cottage in Pittsfield. Enjoy free WiFi, a water park, and a garden. Popular attractions King Park and John Greene Shastid House are located ...
Pine Lakes Outdoor Adventure | Cabin Stay w/ Waterpark Access
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

Explore a world of travel with Expedia