Pittsfield Holidays

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Your Pittsfield Holiday

Our Pittsfield holiday 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 holiday on Expedia.

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Quincy Regional-Baldwin Field Airport (UIN)
Population
4,500
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Pike County Historic Museum, Old Orchard Country Club and King Park

Top hotels in Pittsfield

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is £61 per night from 10 Aug to 11 Aug
£61
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (234 reviews)
Historic hotel
"Very cool, historic hotel! Very clean and well maintained. Within walking distance of several restaurants and bars. ."

Reviewed on 3 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 £82 per night from 5 Sept to 6 Sept
£82
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
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

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

Griggsville, IL
9.8/10 Exceptional! (74 reviews)
70th Anniversary Celebration
"Everything went so smoothly on check-in and the whole week. Kitchen was well stocked with everything we needed, except kitchen scissors. A minor inconvenience. Laundry facilities were provided and worked great! The pool was heated and delightful So much so the baby napped floating in the pool. The ..."

Reviewed on 1 Aug 2025

Get rates
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
See all 33 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Pittsfield travel package cost?
Cross off another part of the world with our Pittsfield travel packages, which start from just . Pick the flights and hotels that match your travel style. Then, add on one or two enriching experiences for an incredible getaway.
If I'm not able to travel, can I cancel my Pittsfield travel package?
Your situation can change without warning, so yes. You may be able to change or cancel your Pittsfield travel package for free within 24 hours of booking. For older bookings, you can still cancel and rebook, but your car rental company, airline or hotel may impose a charge. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Pittsfield?
Bundle your bookings with Expedia to save big bucks on your next big adventure. With over 550 air carriers and 1,000,000 properties around the globe, your Pittsfield travel package can be customized exactly to suit your travel style. With all that extra money, why not include one or more awesome tours and activities? It's an easy way to unlock even more discounts. That dream holiday to Pittsfield is closer than you thought!
Does Expedia offer Book Now, Pay Later Pittsfield holidays?
Expedia has joined forces with online lender Klarna to make booking your next trip a bit easier on the wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that falls within your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: Like the idea of paying for your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Pittsfield?
It makes sense to stay near the action. Many people favor hotels in the vicinity of popular attractions, like King Park, Old Orchard Country Club and John Greene Shastid House.
What are the top hotels in Pittsfield?
Book a stay at William Watson Hotel. It's one of this area's most popular properties. Another highly rated option in Pittsfield is Green Acres Hotel.
How far in advance should I book my Pittsfield holiday?
While prices do change, we generally recommend booking your holiday as early as possible. Most international fares become available on Expedia up to a year in advance. If you're booking last minute, you might still get lucky. Cheaper tickets to Pittsfield sometimes occur in the weeks prior to departure.
What does an Expedia Pittsfield travel package include?
It all comes down to what kind of trip you have in the works. Pittsfield travel deals can include hotels, car rentals and flights. You can mix and match to find the package that suits your needs. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Pittsfield travel package?
You'll pick up terrific savings when you combine your hotels, flights and rental cars into a package. Not just that, booking everything in one place just makes things easier. So why waste time or money? Whether you're putting together a ritzy city getaway or an affordable family break, explore our travel packages today.
Can I choose my airline with a Pittsfield Expedia travel package?
Yes, and with more than 550 airlines to choose from throughout the world, you've got lots of choice. Look through the available options and find out which airline suits your needs and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.