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

Peek'n Peak Resort Trademark Collection by Wyndham
Peek'n Peak Resort Trademark Collection by Wyndham
3.5 out of 5
1405 Olde Road, Clymer, NY
Fully refundableReserve now, pay when you stay
The price is S$149 per night from 3 Aug to 4 Aug
S$149
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (915 reviews)
"Amanda is amazing!!!"

Reviewed on 9 Jul, 2025

Peek'n Peak Resort Trademark Collection by Wyndham
La Quinta Inn & Suites by Wyndham Jamestown
La Quinta Inn & Suites by Wyndham Jamestown
3 out of 5
200 W 3rd St, Jamestown, NY
Fully refundableReserve now, pay when you stay
The price is S$152 per night from 16 Jul to 17 Jul
S$152
16 Jul - 17 Jul
includes taxes & fees
8.4/10 Very Good! (1,014 reviews)
"Very nice location. Within walking distance to many local attractions."

Reviewed on 9 Jul, 2025

La Quinta Inn & Suites by Wyndham Jamestown
Clarion Pointe Jamestown - Falconer
Clarion Pointe Jamestown - Falconer
2.5 out of 5
2800 North Main Street EXT, Jamestown, NY
Fully refundableReserve now, pay when you stay
The price is S$174 per night from 10 Aug to 11 Aug
S$174
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (896 reviews)
Friendly staff and receive pets
"All the staff were kind and friendly. Good quality but basic breakfast. Everything worked well but some renovations could be done in bathrooms."

Reviewed on 8 Jul, 2025

Clarion Pointe Jamestown - Falconer
See all 425 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'll find cheap prices on Expedia for your Pittsfield getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
If you'd like to score a cheap Pittsfield holiday package, consider planning a trip in January, February and March. You're likely to find lower prices on accommodation and flights during these quieter months --- perfect for a budget-friendly getaway.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to see the main attractions during your Pittsfield holiday. But if you prefer to have some time to rest or take day tours, think about extending your trip.
How to find the best Pittsfield package deals?
Start your search for a Pittsfield package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Pittsfield package deal right away, just switch up your dates and search again. Bear in mind 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?
You can enjoy significant savings on your next Pittsfield escape by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Pittsfield?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Pittsfield adventure.
How to plan a trip to Pittsfield?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Pittsfield.
  2. Budget wisely: In addition to the price of your stay, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Pittsfield.
  3. Decide how long to go away for: Now that you're up to speed on Pittsfield, you can work out the ideal length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Pittsfield holiday package that brings all your bookings together.

* 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.