Pittsfield Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Pittsfield
William Watson Hotel
105 East Washington Street Pittsfield IL
S$117
18 Aug - 19 Aug
includes taxes & fees
9.2/10 Wonderful! (368 reviews)
"Our room was not well maintained. The carpet was dirty and frayed. The bathroom tile needs maintenance"
Reviewed on 6 Aug, 2026
Rodeway Inn Pittsfield
1238 W Washington St Pittsfield IL
S$79
30 Aug - 31 Aug
includes taxes & fees
6.8/10 (141 reviews)
"Staff- checked us in on Thursday. Very pleasant and did what he could to get us a room with two double beds. That is what I booked online at hotels.com. He had to call another guest and get it all worked out. He was great. The kid that worked the weekend. Our keys stopped working for our rooms, and ..."
Reviewed on 9 Aug, 2026
Green Acres Hotel
625 W. Washington Pittsfield IL
S$166
12 Aug - 13 Aug
includes taxes & fees
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)
This private 9-hole course challenges golfers with narrow fairways and water hazards across rolling terrain. Members enjoy practice facilities and a welcoming clubhouse restaurant after their round.
Pike County Historic Museum
10.0/10 (1 review)
Housed in the historic East Ward School, this museum showcases Pike County's heritage through artefacts including wedding dresses, furniture, and a vintage printing press. Open weekend afternoons.
King Park
7.4/10 (3 reviews)
This 7.6-acre community hub offers Pittsfield's main swimming pool, skate park, tennis courts, and a lighted fountain. Relax at one of three picnic shelters while the kids enjoy recreational activities.
John Greene Shastid House
10.0/10 (2 reviews)
Step inside this 1838 home where Abraham Lincoln visited his close friend, John Greene Shastid. Guided tours reveal intimate stories of their friendship through original architectural details and personal anecdotes.
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?
- 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.
- 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.
- 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.
- Bundle your airfare and accommodation: After you've settled on your trip dates and duration, lock in the perfect Pittsfield holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
