Pittsfield

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
The price is €83 per night from 5 Oct to 6 Oct
€83
5 Oct - 6 Oct
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free parking, a fitness centre and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County ...
9.2/10 Wonderful! (376 reviews)
"My room was immaculate and comfortable! The staff was super sweet!! 100/10! Will definitely stay again!"

Reviewed on 27 Sept 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
The price is €57 per night from 1 Nov to 2 Nov
€57
1 Nov - 2 Nov
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi 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 27 Sept 2026

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
The price is €92 per night from 14 Oct to 15 Oct
€92
14 Oct - 15 Oct
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free Wi-Fi, 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 30 Sept 2026

Monroe Street Suites
See all 67 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
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Popular attractions Old Orchard Country Club ...
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 13 Aug 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 holiday home in Pittsfield. Enjoy free Wi-Fi, 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
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 Wi-Fi, 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
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 choices and theatre scene.
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