Book Exclusive Pittsfield Vacation Packages

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Pittsfield flight + hotel packages

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The Junction Inn

The Junction Inn

2 out of 5
per person
Dec. 24 - Dec. 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Quincy (UIN)
Stay at this hotel in Perry. Enjoy free WiFi, free parking, and a 24-hour front desk.
Kennedys Red Barn Inn

Kennedys Red Barn Inn

2.5 out of 5
per person
Dec. 24 - Dec. 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Quincy (UIN)
Stay at this B&B in Perry. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mark Twain Lake and Mark Twain Birthplace State Historic Site are located nearby.

Top Pittsfield hotels deals

Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $167 per night
CA $167
CA $183 total
includes taxes & fees
18 Nov - 19 Nov
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid House are located nearby.
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St, Pittsfield, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $87 per night
CA $87
CA $96 total
includes taxes & fees
8 Dec - 9 Dec
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid House are located nearby.
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is CA $161 per night
CA $161
CA $177 total
includes taxes & fees
24 Nov - 25 Nov
Stay at this 3-star hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County Historic Museum are located nearby.
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

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Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Old Orchard Country Club and King Park are located nearby.
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St, Pittsfield, IL
The price is CA $145 per night
CA $145
CA $159 total
includes taxes & fees
16 Nov - 17 Nov
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions John Greene Shastid House and Pike County Historic Museum are located nearby.
Upgraded farmhouse between Springfield Illinois and St.Lous Missouri

Upgraded farmhouse between Springfield Illinois and St.Lous Missouri

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Stay at this farm stay in Pittsfield. Enjoy air conditioning. Popular attractions King Park and John Greene Shastid House are located nearby.
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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 venues and theater scene.

Old Orchard Country Club

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

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

Pittsfield Vacations

Unwittingly stumbling across somewhere new is exactly what makes traveling so extraordinary, But of course, it never hurts to understand a little about the destination before you rush off. We'll help you find out a few basic details about Pittsfield.

This city sits approximately 60 miles (97 kilometers) west of Springfield, the state capital of Illinois, and 30 miles (48 kilometers) northeast of Bowling Green.

Traveling is all about meeting people, so why not make pals with some of the 5,000 locals who live in this corner of Western Illinois?

Places to visit in Pittsfield

Getting out on the green is a fantastic way to stretch your legs and have a ball. Challenge yourself with a friendly round at Old Orchard Country Club. Want some more options? If the young ones are sick of sightseeing and need some exercise, why not take them on an outing to King Park? It's the ideal spot to play hide and seek and throw a ball around. And that's not all. Ditch the history books! Witness the past come alive at Pike County Historic Museum.

Where do you fly into for Pittsfield?

There's no better feeling than touching down in an entirely new place. If you're jumping on a plane to Pittsfield, there's a good chance you'll be disembarking at Abraham Lincoln Capital Airport (SPI). It's roughly 60 miles (97 kilometers) to the east of the main streets. Grab your bags and get set to kick-start your adventure!

Frequently asked questions

How much are vacation packages to Pittsfield?
Starting as low as CA $1,576, flight and hotel packages are a great way to make your budget stretch further. Pittsfield, here you come!
How long should my Pittsfield vacation be?
If you need some guidance, most travelers spend roughly 2 nights vacationing in Pittsfield. But to uncover the true essence of this place, stay a bit longer. That way you can explore more and really soak up the local vibe.
Where can I get the best vacation package deals for Pittsfield?
For a fun and affordable package deal to Pittsfield, nothing compares to Travelocity. Select from 400 airlines and 1,000,000 properties worldwide to create the ideal trip — it couldn’t be easier than that.
Why should I book my Pittsfield vacation bundle with Travelocity?
You’ll not only enjoy big savings, but you’ll also have access to our round-the-clock support, quality service and a Price Match Guarantee. Journey across the globe, uncover hidden treasures and make lifelong memories — we’ll take care of the important details.
Will I save money on my Pittsfield car rental if I book it with my hotel or flight?
Combining your car, hotel and flight into a Pittsfield vacation package is an easy way to score an incredible deal. Plus, having your own set of wheels gives you freedom to find your way to all those big-name sights you want to check out. Sitting 121 kilometers away from Pittsfield, Busch Stadium is one attraction that should be on your to-do list. Fasten your seat belt and make a day trip of it.
Which airport is best for Pittsfield?
That would be Quincy Regional-Baldwin Field Airport (UIN), around 48 kilometers northwest of central Pittsfield.
What is there to do in Pittsfield?
You’ll sense a certain magic as you roam the streets of Pittsfield. Old Orchard Country Club and Pike County Historic Museum are just two renowned sights that make this city so popular, so add them to your itinerary.
Where should I stay when visiting Pittsfield?
The Green Acres Hotel is the first choice of many visitors. Book soon before it’s too late.

Photos of local treasures

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Pittsfield