Pittsfield Vacations from $954

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The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
Price was $1,119, price is now $954 per person
$954
per person
Jul 25 - Aug 1
just found
Roundtrip flight included
San Francisco (SFO) to Jamestown (JHW)
7.2/10 Good! (211 reviews)
The room was in good condition but I would not stay there again. The pool was broke and the hot tub did not bubble!

Reviewed on Feb 23, 2026

3314 Highland Ave. 4 Bedroom Home by RedAwning

3314 Highland Ave. 4 Bedroom Home by RedAwning

3.5 out of 5
Price was $2,840, price is now $2,571 per person
$2,571
per person
Jul 25 - Aug 1
just found
Roundtrip flight included
San Francisco (SFO) to Jamestown (JHW)
No reviews
Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
Price was $1,326, price is now $1,231 per person
$1,231
per person
Jul 25 - Aug 1
just found
Roundtrip flight included
San Francisco (SFO) to Jamestown (JHW)
9.2/10 Wonderful! (816 reviews)
Clean, quiet, good breakfast, easy check in and parking, good location

Reviewed on May 4, 2026

Clarion Pointe Jamestown - Falconer

Clarion Pointe Jamestown - Falconer

2.5 out of 5
Price was $1,070, price is now $1,041 per person
$1,041
per person
Jul 25 - Aug 1
just found
Roundtrip flight included
San Francisco (SFO) to Jamestown (JHW)
8/10 Very Good! (990 reviews)
There could be more outside trash cans Dogs staying there is fine. I had a dog with me but people let their dog crap and left it everywhere. Also smoking outside the doors and cigarette butts all over ground and trash thrown in ground. Disposable coffee or soda cups. I had doggy bags with me at all times because dogs crap. The smoking right outside doors is offensive Inside was clean. Actually I had a canister of disinfectant wipes. Glad I did. The toilet seat looked sketchy. I’m not picky but some things….. The breakfast was the exact same thing everyday Staff was nice

Reviewed on Apr 30, 2026

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

3 out of 5
Price was $1,050, price is now $1,050 per person
$1,050
per person
Jul 25 - Aug 1
just found
Roundtrip flight included
San Francisco (SFO) to Jamestown (JHW)
8.4/10 Very Good! (1,001 reviews)
The room was clean and spacious. Our sink was clogged and because we got into our room quite late we didn’t report it until the morning. Breakfast was good - and hot! They kept everything well stocked and clean

Reviewed on Apr 19, 2026

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Pittsfield Hotel Deals

Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave Celoron NY
$152 nightly
The price is $172 total per night from May 12 to May 13
$172 total
May 12 - May 13
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
Very attentive staff! Great hospitality.

Reviewed on May 5, 2026

Chautauqua Harbor Hotel - Jamestown
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
$88 nightly
The price is $100 total per night from May 14 to May 15
$100 total
May 14 - May 15
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
Breakfast was excellent; staff were extremely courteous and helpful

Reviewed on May 4, 2026

La Quinta Inn & Suites by Wyndham Jamestown
DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

4 out of 5
150 W 4th St Jamestown NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $110 total per night from May 24 to May 25
$110 total
May 24 - May 25
Total with taxes and fees
8.8/10 Excellent! (960 reviews)
Friendly, helpful staff day and evening, nice room, comfortable bed, walking distance to attractions, two restaurants and one bar in house, great security system, no one can get on the floors with rooms or into rooms without a digital guest card, parking garage next door is connected to hotel with ...

Reviewed on May 3, 2026

DoubleTree by Hilton Jamestown
See all 416 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 from $954 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.