Pittsfield Vacations

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Pittsfield Hotel Deals

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
$103 nightly
The price is $116 total per night from Aug 18 to Aug 19
$116 total
Aug 18 - Aug 19
Total includes taxes and fees
8.4/10 Very Good! (954 reviews)
"We enjoyed the peaceful setting. It is dog friendly, which is a plus ($50 extra/night). The property itself deserves some care and maintenance.Some outside areas that look a bit shabby. Several attractions were not open, expect for the pool and zip line."

Reviewed on Aug 4, 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
$101 nightly
The price is $114 total per night from Sep 3 to Sep 4
$114 total
Sep 3 - Sep 4
Total includes taxes and fees
8.2/10 Very Good! (1,003 reviews)
"Staff was very nice and friendly Matt,Paula and their was one more always working with Matt very nice and professional"

Reviewed on Aug 9, 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
$66 nightly
The price is $73 total per night from Aug 14 to Aug 15
$73 total
Aug 14 - Aug 15
Total includes taxes and fees
6.8/10 (1,000 reviews)
"Friendly"

Reviewed on Aug 4, 2025

Days Inn by Wyndham Warren
See all 427 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.

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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 book a cheap Pittsfield vacation package, consider traveling in November, December and January. You'll generally find lower prices on hotels and flights during these months — perfect for budget-conscious travelers.
How many days is enough for Pittsfield?
Typically, a handful of days is enough to explore the top sights during your Pittsfield vacation. However, if you prefer to have time to chill out or go on day tours, think about extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Pittsfield trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.