Pittsfield Vacations

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Find the Best Pittsfield Vacation Packages

Pittsfield Hotel Deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
The price is ￥11,679 per night from Aug 19 to Aug 20
￥11,679
￥12,845 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (236 reviews)
"Always my Go-to place to stay in Pittsfield! Great staff, clean, comfortable, and location. Some rooms do not have windows so are really dark inside. But overall great place to stay!!"

Reviewed on Aug 6, 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 ￥14,626 per night from Sep 5 to Sep 6
￥14,626
￥16,086 total
Sep 5 - Sep 6
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 Jul 23, 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
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 Aug 1, 2025

Get rates
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
See all 34 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.

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?
If you're hoping to snag a cheap Pittsfield vacation package, consider traveling in January, March and April. You'll typically find better prices on hotels and airfares during these months — ideal for travelers 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 vacation. 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 vacation package to Pittsfield?
Pittsfield offers everything you need for an amazing getaway. Begin your Pittsfield vacation 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 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.
How to plan a trip to Pittsfield?

  1. 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 vacation in Pittsfield.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodations: After you've settled on your trip dates and duration, lock in the perfect Pittsfield vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.