Pittsfield Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

Ready to book your vacation to Pittsfield?

 

Choose your dates

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
The price is CA $174 per night from Sep 9 to Sep 10
CA $174
CA $199 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"The staff at front desk were helpful, friendly and professional. The lady who takes care of breakfast did an awesome job, the setup is eye appealing. Food is delicious and plentiful."

Reviewed on Aug. 22, 2025

Best Western Cooperstown Inn & Suites
The Marx Hotel

The Marx Hotel

2.5 out of 5
55 Market St, Oneonta, NY
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Sep 7 to Sep 8
CA $158
CA $183 total
Sep 7 - Sep 8
includes taxes & fees
7/10 Good! (1,000 reviews)
"Beautiful property! Front desk staff did a marvelous job of straightening out our reservation. Rates are very reasonable for a high quality experience"

Reviewed on Aug. 21, 2025

The Marx Hotel
Hampton Inn Cooperstown

Hampton Inn Cooperstown

2.5 out of 5
4882 State Highway 28, Cooperstown, NY
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Sep 7 to Sep 8
CA $210
CA $240 total
Sep 7 - Sep 8
includes taxes & fees
9.8/10 Exceptional! (29 reviews)
"We arrived later than expected, was met by a lovely lady who made our checkin easy! Breakfast was included and was fantastic. The pool was clean, exercise room was well stocked with everything we needed. Clean and quiet hotel."

Reviewed on Aug. 23, 2025

Hampton Inn Cooperstown
See all 988 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a vacation to Pittsfield costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Pittsfield?
Travel in the off-peak season and you're likely to find cheap Pittsfield vacation packages. Remember that school vacation periods and major festivals and events can impact prices, so do some research before booking.
How many days is enough for Pittsfield?
Typically, a handful of days is enough to tick off the major sights during your Pittsfield vacation. However, if you prefer to have more time to kick back or go on day trips, think about extending your trip.
How to find the best Pittsfield package deals?
Use Expedia's handy filters to help you find some tempting Pittsfield package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Pittsfield package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pittsfield vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Pittsfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Pittsfield?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Pittsfield break.
How to plan a trip to Pittsfield?

  1. Choose when to go: Check your schedule and get packing. Your favourite time of year and the type of activities available will also help you decide when to vacation in Pittsfield.
  2. Figure out your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will probably be the largest expense during your trip to Pittsfield.
  3. Decide how long to go away for: Now that you're up to speed on Pittsfield, you can figure out the right length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Combine your accommodations and airfare: Once you've nailed down your trip dates and duration, book the perfect Pittsfield vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.