Deals on vacations and trips to Pittsfield

Save when you book Pittsfield package deals

Choose two or more items and save on your trip:

Pittsfield flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Beardstown

Americas Best Value Inn Beardstown

2 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Quincy (UIN)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Pittsfield hotels deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
$80 nightly
The price is $89 total per night
$89 total
Jul 17 - Jul 18
Total includes taxes and fees
A gym is featured at this hotel, along with free parking. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli is provided and the front desk is staffed around-the-clock.
Parking included
Free WiFi
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $131 total per night
$131 total
Jul 4 - Jul 5
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. A terrace, a garden, and a lobby fireplace are also on offer.
Breakfast included
Parking included
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St, Pittsfield, IL
Free Cancellation
Reserve now, pay when you stay
$62 nightly
The price is $68 total per night
$68 total
Jul 6 - Jul 7
Total includes taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Luggage storage is also provided.
Breakfast included
Pet friendly
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St, Pittsfield, IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $178 total per night
$178 total
Jul 4 - Jul 5
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A communal living room, a picnic area, and locker space are also on offer.
Parking included
Free WiFi
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

Get rates
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Pool
Kitchen
Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

Lakeside Lodge of LEGENDS; A Wilderness Wanderer’s Wonderland

2 out of 5
$331 nightly
The price is $354 total per night
$354 total
Jul 5 - Jul 6
Total includes taxes and fees
Stay at this cabin in Pittsfield. Enjoy air conditioning. Popular attractions Old Orchard Country Club and Pike County Historic Museum are located nearby.
Air conditioning
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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

4.5/5(7 reviews)

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

Illini Community Hospital

Though Illini Community Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Pittsfield while you are here.

Illini Community Hospital

Frequently asked questions

How much are vacation packages to Pittsfield?
Starting as low as $649, 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 75 mi 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 30 mi 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

Browse Pittsfield vacation photos for more inspiration

Pittsfield