Pittsfield Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Pittsfield

Fireside Inn & Suites Waterville
Fireside Inn & Suites Waterville
2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is S$223 per night from 10 Jul to 11 Jul
S$223
10 Jul - 11 Jul
includes taxes & fees
8.6/10 Excellent! (999 reviews)
"Nice place to stay. Pool and hot tub were excellent. We'd stay again"

Reviewed on 8 Jul, 2025

Fireside Inn & Suites Waterville
Holiday Inn Express & Suites Waterville - North by IHG
Holiday Inn Express & Suites Waterville - North by IHG
2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
The price is S$188 per night from 20 Jul to 21 Jul
S$188
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (756 reviews)
"Very clean, quiet and the breakfast was better than most at this tier level. Close to downtown and shops which was convenient. Would stay again."

Reviewed on 23 Jun, 2025

Holiday Inn Express & Suites Waterville - North by IHG
The Elmwood
The Elmwood
2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is S$208 per night from 10 Jul to 11 Jul
S$208
10 Jul - 11 Jul
includes taxes & fees
8.6/10 Excellent! (411 reviews)
"Was clean and comfortable and the accept pets"

Reviewed on 6 Jul, 2025

The Elmwood
See all 233 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.

Popular places to visit

JW Parks Golf Course

Enjoy a round of golf in Pittsfield at JW Parks Golf Course. Make some time to visit the shops while you're in the area.

JW Parks Golf Course

Frequently asked questions

How much does a Pittsfield holiday package cost?
You'll find cheap prices on Expedia for your Pittsfield break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
Travel in the shoulder or low season and you're likely to score cheap Pittsfield holiday packages. Keep in mind that public holidays and major festivals and events can have an impact on prices, so do your research before booking.
How many days is enough for Pittsfield?
The ideal length of your Pittsfield holiday depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to visit all the major attractions and discover some hidden gems along the way.
How to find the best Pittsfield package deals?
Use Expedia's filters to find some terrific Pittsfield package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Pittsfield package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
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 flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the freedom to create a customised Pittsfield holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Pittsfield?
If you have your Pittsfield travel dates finalized, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Pittsfield?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Pittsfield.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodation will probably be the largest expense during your trip to Pittsfield.
  3. Decide how long to go for: Now that you're up to speed on Pittsfield, you can figure out the right length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Combine your airfare and accommodation: After you've nailed down your trip dates and duration, book the ideal 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.