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
$104 nightly
The price is $117 total per night from Feb 23 to Feb 24
$117 total
Feb 23 - Feb 24
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
Great location!

Reviewed on Feb 20, 2026

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
$85 nightly
The price is $96 total per night from Feb 23 to Feb 24
$96 total
Feb 23 - Feb 24
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
Room was clean,staff was great but breakfast choices were the worst of any hotel I’ve been at. There wasn’t many places to park for having as many rooms as they have.

Reviewed on Feb 18, 2026

La Quinta Inn & Suites by Wyndham Jamestown
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave Celoron NY
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Feb 25 to Feb 26
$124 total
Feb 25 - Feb 26
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
Easy check-in and beautiful room. We did not expect the beautiful view that came with the room!! 5 Stars!!

Reviewed on Feb 2, 2026

Chautauqua Harbor Hotel - Jamestown
See all 419 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.

Find the Best Pittsfield Vacation Packages

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Top Sights
Chapman State Park and Warren County Historical Society

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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.