Pittsfield Holidays

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Pittsfield Holiday

Our pick of the best Pittsfield Hotel Deals

William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
The price is NZ$164 per night from 11 July to 12 July
NZ$164
11 July - 12 July
includes taxes & fees
9.2/10 Wonderful! (364 reviews)
"The check-in process was extremely easy. The atmosphere was wonderful, clean rooms, we loved everything about the hotel!"

Reviewed on 21 June 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
The price is NZ$117 per night from 13 July to 14 July
NZ$117
13 July - 14 July
includes taxes & fees
6.8/10 (139 reviews)
"Don’t do it!!!! Trust me. No soap, no ice, hardly AC. Would not get into shower for at all. Terrible"

Reviewed on 18 June 2026

Rodeway Inn Pittsfield
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St Pittsfield IL
The price is NZ$188 per night from 6 July to 7 July
NZ$188
6 July - 7 July
includes taxes & fees
9.6/10 Exceptional! (65 reviews)
"Staff was wonderful Room were clean and nicely decorated Very quite building with no street noise Safe neighbourhood Lots of historic bldgs in town"

Reviewed on 12 June 2026

Monroe Street Suites
See all 65 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.

Stay near popular Pittsfield attractions

Old Orchard Country Club

8.8/10 (8 reviews)
This private 9-hole course challenges golfers with narrow fairways and water hazards across rolling terrain. Members enjoy practice facilities and a welcoming clubhouse restaurant after their round.
See properties

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.

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