Pittsfield Vacations from $166

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Your Pittsfield Vacation

Skip the stress of organizing your next great adventure with a Pittsfield vacation package. Whether you're visiting for its cuisine, history, art or something else, there's a never-ending supply of new experiences to be had. Fill your trip to Pittsfield with visits to some of its top attractions. First stop? Make it Unadilla Motocross. A couple of quick clicks is all it takes to craft the ideal Pittsfield vacation on Expedia.

The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Jeannies Dream Motel

Jeannies Dream Motel

2 out of 5
Price was $189, price is now $166 per person
$166
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rome (RME)
10.4/10 Exceptional! (25 reviews)
Perfect little spot to stay while working in the area! Great price and the room was exactly what we needed.

Reviewed on Sep 1, 2025

Colgate Inn

Colgate Inn

4 out of 5
Price was $478, price is now $408 per person
$408
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rome (RME)
18.8/10 Exceptional! (195 reviews)
Homewood Suites by Hilton New Hartford Utica

Homewood Suites by Hilton New Hartford Utica

3 out of 5
Price was $395, price is now $359 per person
$359
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rome (RME)
18.8/10 Exceptional! (510 reviews)
Excellent hotel. Great staff great room.

Reviewed on Nov 20, 2025

Hampton Inn and Suites New Hartford/Utica

Hampton Inn and Suites New Hartford/Utica

2.5 out of 5
Price was $351, price is now $320 per person
$320
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rome (RME)
18.4/10 Exceptional! (1,000 reviews)
Sam at the desk was the GOAT. Enjoyed our stay.

Reviewed on Oct 12, 2025

Major League Motor Inn

Major League Motor Inn

2 out of 5
Price was $343, price is now $316 per person
$316
per person
Jan 9 - Jan 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rome (RME)
18/10 Exceptional! (2 reviews)
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Discover the most popular places to visit in Pittsfield

Unadilla Motocross

You can take time to visit Unadilla Motocross during your travels to New Berlin.

Unadilla Motocross

Pittsfield Hotel Deals

Best Western Cooperstown Inn & Suites

Best Western Cooperstown Inn & Suites

2.5 out of 5
50 Commons Drive Cooperstown NY
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $103 total per night from Dec 7 to Dec 8
$103 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Uncomfortable beds and the hot tub was up way to high

Reviewed on Nov 16, 2025

Best Western Cooperstown Inn & Suites
Hampton Inn Cooperstown

Hampton Inn Cooperstown

2.5 out of 5
4882 State Highway 28 Cooperstown NY
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $121 total per night from Nov 30 to Dec 1
$121 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (92 reviews)
Stayed 4 nights. Room was very clean. Very good location, Ten minutes to downtown Cooperstown. Free breakfast and coffee good, just stay away from the ‘eggs’.

Reviewed on Nov 19, 2025

Hampton Inn Cooperstown
Holiday Inn Express Oneonta by IHG

Holiday Inn Express Oneonta by IHG

2.5 out of 5
141 COURTYARD DRIVE Oneonta NY
Fully refundable
$95 nightly
The price is $109 total per night from Dec 13 to Dec 14
$109 total
Dec 13 - Dec 14
Total with taxes and fees
9.4/10 Exceptional! (825 reviews)
Room was spotless, staff was friendly & great breakfast options!

Reviewed on Nov 17, 2025

Holiday Inn Express Oneonta by IHG
See all 981 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

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You'll find cheap prices from $166 on Expedia for your Pittsfield escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
If you're looking to score a cheap Pittsfield vacation package, consider planning a trip in November, December and January. You'll generally find better rates on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Pittsfield?
Generally, a handful of days is enough to go to the major attractions during your Pittsfield vacation. However, if you want to have some time to relax or take day tours, think about extending your trip.
How to find the best Pittsfield package deals?
Begin your search for a Pittsfield package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Pittsfield package deal right away, just tweak 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?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can tailor your Pittsfield escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pittsfield?
If you're planning a spur-of-the-moment Pittsfield getaway, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield break should be a relaxing escape from your busy life, not a reason for money worries. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.