Pittsfield Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Pittsfield

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$92 per night from 8 Dec to 9 Dec
S$92
includes taxes & fees
8 Dec - 9 Dec
6.8/10 (111 reviews)
Oldie and Pretty Goodie
"This motel is more than 70 years old. The owners have made significant upgrades to a very old motel. Room looks nice upon entry and it was impeccably clean. The bed was possibly the best i have encountered in years. What you cant change are 2 foot by 2 foot showers, and a lack of heating controls ..."

Reviewed on 21 Oct,2024

Rodeway Inn
William Watson Hotel
William Watson Hotel
3 out of 5
105 East Washington Street, Pittsfield, IL
The price is S$165 per night from 24 Nov to 25 Nov
S$165
includes taxes & fees
24 Nov - 25 Nov
9.2/10 Wonderful! (219 reviews)
"Very comfortable, home, atmosphere. The staff was great!!!! Couldn’t ask for a better place to stay!"

Reviewed on 14 Nov,2024

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$176 per night from 30 Nov to 1 Dec
S$176
includes taxes & fees
30 Nov - 1 Dec
8.4/10 Very Good! (117 reviews)
"Have stayed twice at Green Acres Hotel. Family run. V"

Reviewed on 28 Jul,2024

Green Acres Hotel
See all 31 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?
The most affordable Pittsfield holiday package is , so your dream getaway can become a reality — without spending an arm and a leg. Bundle flights, hotels and car rentals to tailor make a package suited to your travel style.
How do I get a cheap travel package to Pittsfield?
Bundle your flight and hotel bookings, add extras such as tours, and save with a Pittsfield holiday package. You won’t just pick up superb discounts on your getaway — you’ll have loads of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 air carriers and 1,000,000 properties throughout the world. Your next epic adventure begins right here, right now!
Where should I stay in Pittsfield?
With fascinating attractions such as Old Orchard Country Club and Pike County Historic Museum in this neighbourhood, try to find a hotel situated near them. King Park is another Pittsfield hot spot that travellers flock to.
What are the top hotels in Pittsfield?
If this will be your first time in Pittsfield, make a reservation at William Watson Hotel or Green Acres Hotel. Both hotels offer friendly service and are top options with many travellers.
How far in advance should I book my Pittsfield holiday?
It can be difficult to know when the best time is to book your trip to Pittsfield. But typically the earlier you book, the lower the prices. Sometimes, you can book your flights and hotels nearly 12 months before your departure date. If you’re hoping for a last-minute getaway, no need to fret! There are incredible deals advertised on Expedia every single day.
What does an Expedia Pittsfield travel package include?
Rental cars, flights and hotels — we’ve got them covered. With Expedia, you can shape your Pittsfield travel package the way you want. All you have to do is determine just what you need. Once you’ve made your booking, you can add on extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Pittsfield travel package?
You’ll pick up impressive savings when you combine your hotels, flights and rental cars into a package. Not only that, booking everything in one place just makes things easier. So why waste your money or time? Whether you’re organising a ritzy romantic getaway or a budget family adventure, check out our package deals today.
Can I choose my airline with a Pittsfield Expedia holiday package?
Yes — that’s one of the best things about an Expedia package. You’re in control. We have more than 550 airline partners throughout the world, so you have options galore when organising your Pittsfield trip.
If I'm not able to travel, can I cancel my Pittsfield holiday package?
Don’t stress if you’re rethinking your Pittsfield holiday package — it’s possible to cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally understand life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that occurs. When you’re ready to make changes, we’re here to help.

* 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.