Pittsfield Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Pittsfield

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is 2.228.020 ₫ per night from 7 Sept to 8 Sept
2.228.020 ₫
2.450.376 ₫ total
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (236 reviews)
"Always my Go-to place to stay in Pittsfield! Great staff, clean, comfortable, and location. Some rooms do not have windows so are really dark inside. But overall great place to stay!!"

Reviewed on 6 Aug 2025

William Watson Hotel
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Fully refundableReserve now, pay when you stay
The price is 2.597.364 ₫ per night from 5 Sept to 6 Sept
2.597.364 ₫
2.856.576 ₫ total
5 Sept - 6 Sept
includes taxes & fees
8.6/10 Excellent! (134 reviews)
"Wonderful stay - was staying with a number of family members and it all worked out"

Reviewed on 23 Jul 2025

Green Acres Hotel
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St, Pittsfield, IL
Fully refundableReserve now, pay when you stay
The price is 1.515.326 ₫ per night from 2 Sept to 3 Sept
1.515.326 ₫
1.666.555 ₫ total
2 Sept - 3 Sept
includes taxes & fees
6.8/10 (118 reviews)
"They really should attach the drain cover to the shower drain. Somebody could get seriously injured. Being a tile guy, looking around really had me laughing at the workmanship. The manager was a pretty cool guy, the room was fine, air conditioner worked great. Never went to the continental breakfast, ..."

Reviewed on 7 Jul 2025

Rodeway Inn
See all 34 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.

Popular places to visit

Old Orchard Country Club

Enjoy a round of golf in Pittsfield at Old Orchard Country Club. Experience the area's entertainment choices and theatre scene.

Old Orchard Country Club

Pike County Historic Museum

You can study the exhibits at Pike County Historic Museum, a museum with a storied past, during your travels to Pittsfield. Experience the area's entertainment choices and theatre scene.

Pike County Historic Museum

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 choices and theatre scene.

John Greene Shastid House

Frequently asked questions

How much does a Pittsfield holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Pittsfield costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Pittsfield?
If you're hoping to snag a cheap Pittsfield holiday package, consider travelling in January, March and April. You'll typically find better prices on hotels and airfares during these months — ideal for travellers wishing to save money.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to visit the top sights during your Pittsfield holiday. But if you'd like to have more time to kick back or take day tours, think about extending your trip.
Is it worth booking a holiday package to Pittsfield?
Pittsfield offers everything you need for an amazing getaway. Begin your Pittsfield holiday on a high note by checking out popular attractions like Old Orchard Country Club.
How to find the best Pittsfield package deals?
Begin your search for a Pittsfield package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Pittsfield package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pittsfield getaway off to a flying start.
Is it cheaper to book a Pittsfield holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still get the flexibility to create a tailored Pittsfield holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Pittsfield?
If you're planning a spur-of-the-moment Pittsfield trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Pittsfield?

  1. Choose when to get away: Check your schedule and get your bags packed. Your preferred season and the activities on offer will also help you decide when to holiday in Pittsfield.
  2. Budget wisely: As well as the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Pittsfield.
  3. Decide your trip length: Consider how long you'd like to spend discovering Pittsfield. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodation: After you've settled on your trip dates and duration, lock in the perfect Pittsfield holiday package for you.