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

Find all hotels by Wyndham Hotels in Pittsfield, IL

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Best place Ive stayed period. 100 percent recommend"
Isidro 2-night trip
Posted 2 days ago
Monroe Street Suites
William Watson Hotel

William Watson Hotel

10/10 Excellent
"My room was immaculate and comfortable! The staff was super sweet!! 100/10! Will definitely stay again!"
Mary 2-night trip
Posted 5 days ago
William Watson Hotel
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

10/10 Excellent
"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 much. Just as great was the tennis court with Pickleball area and basketball court. Our group also made good use of the game room with billiards, ping-pong, foosball. This is a very fine oasis with something for everyone to do!"
John Z. 6-night trip
Posted 2 months ago
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

10/10 Excellent
"Communication"
Sabrina 7-night trip
Posted 4 months ago
Rodeway Inn Pittsfield

Explore a world of travel with Expedia