Pittsfield Vacations

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Your Pittsfield Vacation

Our Pittsfield vacation packages give you endless opportunities to enjoy new sights, sounds and tastes. And with all the planning taken care of, you can breathe easy and enjoy your city adventure without a worry in the world. Every trip to Pittsfield needs a well-thought-out itinerary. Fill yours with leading attractions like Old Orchard Country Club, John Greene Shastid House and Pike County Historic Museum. A couple of quick clicks is all it takes to craft a tailor-made Pittsfield vacation on Expedia.

Discover the most popular places to visit in Pittsfield

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.

Old Orchard Country Club

Pike County Historic Museum

You can study the exhibits at Pike County Historic Museum, a museum with a story of its own, during your travels to Pittsfield. Experience the area's entertainment venues and theater 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 venues and theater scene.

John Greene Shastid House

Pittsfield Hotel Deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
$78 nightly
The price is $86 total per night from May 7 to May 8
$86 total
May 7 - May 8
Total with taxes and fees
9.2/10 Wonderful! (354 reviews)
Enjoyable and pleasant surroundings. The quaint hotel is located on the town square with an in-house restaurant and shops and a great pizza parlor close by. Everyone was friendly and helpful.

Reviewed on Apr 29, 2026

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
$117 nightly
The price is $129 total per night from May 3 to May 4
$129 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (145 reviews)
A nice, cozy, small town feel. Was recommended Gianni's pizza down the road from the hotel staff. Very friendly people, will stay again when I visit

Reviewed on Apr 30, 2026

Green Acres Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
$59 nightly
The price is $65 total per night from May 17 to May 18
$65 total
May 17 - May 18
Total with taxes and fees
Rodeway Inn Pittsfield
See all 64 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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Quincy Regional-Baldwin Field Airport (UIN)
Population
4,500
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Pike County Historic Museum, Old Orchard Country Club and John Greene Shastid House

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation to Pittsfield costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Pittsfield?
January, February and April are great times to look for cheap Pittsfield vacation packages. Choosing to travel in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Pittsfield?
The ideal duration of your Pittsfield vacation depends on what you'd like to do. Generally, a handful of days to a week will give you time to hit all the major sights and discover some hidden treasures along the way.
Is it worth booking a vacation package to Pittsfield?
It's no wonder a Pittsfield vacation is on the must-do list of many travelers. Well-known attractions like Old Orchard Country Club are just the start of things to see and do here.
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 vacation as a package?
Expedia vacation 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 vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield break is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.