Pittsfield Trips (flight + hotel)

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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 P4,373 per night from Aug 12 to Aug 13
P4,373
P6,662 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (946 reviews)
"I like this place always"

Reviewed on Jul 30, 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
The price is P5,803 per night from Sep 3 to Sep 4
P5,803
P6,557 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"All of the staff were friendly and helpful. The rooms were clean. very convenient location. Limited parking."

Reviewed on Aug 1, 2025

La Quinta Inn & Suites by Wyndham Jamestown
Days Inn by Wyndham Warren

Days Inn by Wyndham Warren

3 out of 5
210 Ludlow Street, Warren, PA
Fully refundableReserve now, pay when you stay
The price is P3,535 per night from Sep 1 to Sep 2
P3,535
P3,924 total
Sep 1 - Sep 2
includes taxes & fees
6.8/10 (1,005 reviews)
"Rooms are being beautifully renovated. So impressed with the upgrades! Was a little disappointed the continental breakfast was on pause due to the renovations and wish the pool was kept warm enough to enjoy. I have been coming to this hotel for 30+ years to visit family, and I’m so happy to see it ..."

Reviewed on Jul 21, 2025

Days Inn by Wyndham Warren
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 vacation 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 vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
If you'd like to score a cheap Pittsfield vacation package, consider planning a trip in January, February and March. You're likely to find lower prices on accommodations 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 vacation. 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 vacation as a package?
You can enjoy significant savings on your next Pittsfield escape by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation 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, favorite 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 vacation. 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 vacation 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.