Pittsfield Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Ready to book your vacation to Pittsfield?

 

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Pittsfield Hotel Deals

Oneida Casino Hotel
Oneida Casino Hotel
3.5 out of 5
2040 Airport Dr, Green Bay, WI
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 27 to Jul 28
CA $127
CA $147 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (1,032 reviews)
"Was given a secluded room that was extremely quiet!"

Reviewed on Jul. 13, 2025

Oneida Casino Hotel
Tundra Lodge
Tundra Lodge
3.5 out of 5
865 Lombardi Ave, Green Bay, WI
The price is CA $189 per night from Jul 29 to Jul 30
CA $189
CA $255 total
Jul 29 - Jul 30
includes taxes & fees
7.4/10 Good! (1,324 reviews)
"We had a great time and I was pleasantly surprised."

Reviewed on Jul. 10, 2025

Tundra Lodge
Hotel J Green Bay
Hotel J Green Bay
2 out of 5
2620 S. Packerland Dr, Green Bay, WI
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Jul 30 to Jul 31
CA $120
CA $139 total
Jul 30 - Jul 31
includes taxes & fees
9/10 Wonderful! (1,116 reviews)
"Our room was spotless! Was also very quiet. I would recommend this hotel to friends."

Reviewed on Jul. 11, 2025

Hotel J Green Bay
See all 638 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?
You can grab a vacation package to this popular destination on Expedia. But how much your vacation to Pittsfield costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Pittsfield?
If you're looking to book a cheap Pittsfield vacation package, consider planning a trip in January, February and April. You'll usually find better rates on flights and hotels during these quieter months --- perfect for a budget-friendly break.
How many days is enough for Pittsfield?
Usually, a handful of days is enough to see the top attractions during your Pittsfield vacation. But if you'd like to have some time to kick back or go on day trips, think about extending your itinerary.
How to find the best Pittsfield package deals?
Bagging a cheap Pittsfield package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Pittsfield package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pittsfield?
If you have your Pittsfield vacation dates confirmed, book as soon as you can to score some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Pittsfield?

  1. Choose when to travel: Check your diary and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Pittsfield.
  2. Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Pittsfield.
  3. Decide your trip length: Consider how long you'd like to spend discovering Pittsfield. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Pittsfield vacation package that brings all your bookings together.

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