Pittsfield Holidays

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Top hotels in Pittsfield

William Watson Hotel
William Watson Hotel
3 out of 5
105 East Washington Street, Pittsfield, IL
The price is S$111 per night from 17 Jun to 18 Jun
S$111
17 Jun - 18 Jun
includes taxes & fees
9.4/10 Exceptional! (225 reviews)
"Nice clean rooms. The room had nice unique decor. Comfortable feeling."

Reviewed on 2 Jun, 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 S$168 per night from 16 Jun to 17 Jun
S$168
16 Jun - 17 Jun
includes taxes & fees
8.6/10 Excellent! (126 reviews)
"Great stay"

Reviewed on 3 Jun, 2025

Green Acres Hotel
Rodeway Inn
Rodeway Inn
2 out of 5
1238 W Washington St, Pittsfield, IL
Fully refundableReserve now, pay when you stay
The price is S$86 per night from 22 Jun to 23 Jun
S$86
22 Jun - 23 Jun
includes taxes & fees
6.8/10 (116 reviews)
"Great little hotel, perfect for an overnight pit stop"

Reviewed on 28 May, 2025

Rodeway Inn
See all 30 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 holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday 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 holiday package, consider travelling in January, March and April. You’ll typically find better prices on hotels and airfares during these months — ideal for travellers 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 holiday. 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 holiday package to Pittsfield?
Pittsfield offers everything you need for an amazing getaway. Begin your Pittsfield holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 holiday 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 accommodation: After you’ve settled on your trip dates and duration, lock in the perfect Pittsfield holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.