Find hotels in Pittsfield, IL from ￥10,544

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
Dec 12 - Dec 13
Tomorrow
Dec 13 - Dec 14
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pittsfield hotels

Breakfast meal
William Watson Hotel

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (346)
William Watson Hotel welcomes guests with a fitness center and convenient snack bar. Enjoy nearby John Greene Shastid House and Pike County Historic Museum, plus 24-hour front desk service. Quincy Regional Airport is just an hour's drive away.
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is ￥13,085
￥14,391 total
includes taxes & fees
Dec 13 - Dec 14
William Watson Hotel
Free daily on-the-go breakfast
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (125)
Conveniently situated in Pittsfield near King Park and John Greene Shastid House, this hotel offers free WiFi, parking, and daily on-the-go breakfast. Guests enjoy comfortable rooms with easy access to local attractions.
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveler
The price is ￥9,656
￥10,619 total
includes taxes & fees
Dec 15 - Dec 16
Rodeway Inn Pittsfield
Free daily continental breakfast
Green Acres Hotel

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
Green Acres Hotel offers a relaxing stay near King Park and John Greene Shastid House. Enjoy the complimentary continental breakfast served daily, plus free WiFi and parking. This comfortable hotel provides the perfect base for exploring Pittsfield attractions.
"Great stay"
United States
Jeramy
The price is ￥16,653
￥18,314 total
includes taxes & fees
Dec 14 - Dec 15
Green Acres Hotel
Hallway
Monroe Street Suites

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
Cozy accommodations in Pittsfield with convenient access to John Greene Shastid House and Pike County Historic Museum. This hotel offers complimentary WiFi, free parking, and daily housekeeping for a comfortable, hassle-free stay.
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is ￥13,411
￥14,750 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Monroe Street Suites
Interior
The Eagles Nest Inn

The Eagles Nest Inn

The Eagles Nest Inn
3.0 star property
Louisiana
9.4 out of 10, Exceptional, (19)
Italian cuisine awaits at Gambino's Eatery in this cozy Louisiana inn. After exploring the nearby Mississippi River, unwind in a plush bathrobe. Free WiFi and parking enhance your stay.
"The room was great. Large and attractive!! Nice bathroom. Had all the convenience you need from TV to mini frig. "
United States
Judith
The price is ￥14,868
￥16,881 total
includes taxes & fees
Dec 13 - Dec 14
The Eagles Nest Inn
Property grounds
River's Edge Motel

River's Edge Motel

River's Edge Motel
2.0 star property
Louisiana
9.0 out of 10, Wonderful, (355)
Enjoy Southern hospitality at this welcoming Louisiana establishment. The 24-hour front desk ensures round-the-clock service, while complimentary WiFi keeps you connected. Guests consistently praise the helpful staff and convenient amenities.
"Excellent stay !!! Quite "
United States
Bradley
The price is ￥12,439
￥14,123 total
includes taxes & fees
Dec 22 - Dec 23
River's Edge Motel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Pittsfield attractions

Old Orchard Country Club

Enjoy a round of golf in Pittsfield at Old Orchard Country Club. Experience the area's entertainment venues and theater scene.
See properties

John Greene Shastid House

You can browse the exhibits at John Greene Shastid House, a museum with a storied past, during your travels to Pittsfield. Experience the area's entertainment venues and theater scene.
See properties

Learn more about Pittsfield

Nestled among rolling hills, Pittsfield invites history buffs to explore the John Greene Shastid House and Pike County Historic Museum. After delving into local heritage, visitors can unwind with a peaceful afternoon at King Park or tee off at nearby Old Orchard Country Club.

See all hotels in Pittsfield
Court House in Pittsfield

Top Pittsfield Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Wonderful stay right on the town square with Christmas music playing. Felt a little like I was staying in Stars Hollow. Lovely people in this small town."
Lynn 1-night trip
Posted 3 days ago
William Watson Hotel

More cheap stays in Pittsfield

Rodeway Inn

Rodeway Inn

1238 W Washington St Pittsfield IL
The price is ￥9,587 per night from Dec 14 to Dec 15
￥9,587
￥10,544 total
Dec 14 - Dec 15
includes taxes & fees
6.6/10 (125 reviews)

Frequently asked questions

Where is the best place for a stay in Pittsfield?
Monroe Street Suites is a favorite property for Expedia customers. This hotel offers free parking and free WiFi. Traveler reviews also recommend William Watson Hotel and Green Acres Hotel as top choices for your stay. See all available top hotels, or vacation rentals in Pittsfield.
What's the top vacation rental that Pittsfield has to offer?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This Pittsfield vacation home rental is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, you'll find most room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
Where can I learn more about changing or cancelling my trip to Pittsfield?
For more information about picking new dates or cancelling your trip to Pittsfield, click here.
What is the favorite LGBTQ-friendly hotel in Pittsfield?
William Watson Hotel is a top LGBTQ-friendly hotel that features free parking and a fitness center. See all available hotels listed as LGBTQ-friendly in Pittsfield.
What's the best pet-friendly place to stay in Pittsfield?
Rodeway Inn is a top hotel for people traveling with their pets, and offers free WiFi for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
Where is the best hotel to stay near Old Orchard Country Club?
Green Acres Hotel is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. It's located 2.4 mi (3.9 km) from Old Orchard Country Club. Other good choices within 5 miles include William Watson Hotel and Monroe Street Suites.
What are some accommodations with pools in Pittsfield?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: Features sun loungers, a pool, and complimentary wireless internet access. View all hotels with pools in Pittsfield.
How is it to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer including the cafes, entertainment choices, and breweries. Tourists can also enjoy so much more including its theaters. In Pittsfield, there are 10 hotels and other accommodations to choose from. Find out more about Pittsfield.
What is there to see in Pittsfield?
Cultural venues include John Greene Shastid House and Pike County Historic Museum. A couple of additional sights to add to your agenda are Old Orchard Country Club and King Park. Check out what more to see and do in Expedia's Pittsfield guide.
What's the weather like in Pittsfield?
The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Pittsfield is 46 inches.

Explore a world of travel with Expedia