Pittsfield Vacations from $511

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The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Cobblestone Inn & Suites-Fremont

Cobblestone Inn & Suites-Fremont

2.5 out of 5
Price was $590, price is now $511 per person
$511
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Appleton (ATW)
9/10 Wonderful! (288 reviews)
Like many places anywhere, short staffed. The staff was helpful. Breakfast was not good.

Reviewed on Aug 26, 2025

Days Inn by Wyndham Neenah

Days Inn by Wyndham Neenah

2 out of 5
Price was $686, price is now $605 per person
$605
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Green Bay (GRB)
7.4/10 Good! (746 reviews)
A quiet place to rest after work

Reviewed on Aug 21, 2025

DoubleTree by Hilton Neenah

DoubleTree by Hilton Neenah

4 out of 5
Price was $1,144, price is now $1,018 per person
$1,018
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Green Bay (GRB)
8.6/10 Excellent! (968 reviews)
This place is how all motels should be. Everything was perfect.

Reviewed on Aug 24, 2025

Sleep Inn & Suites Green Bay South

Sleep Inn & Suites Green Bay South

2.5 out of 5
Price was $770, price is now $685 per person
$685
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Green Bay (GRB)
8.6/10 Excellent! (913 reviews)
The room was large enough for our group

Reviewed on Aug 25, 2025

AmericInn by Wyndham New London

AmericInn by Wyndham New London

2.5 out of 5
Price was $611, price is now $550 per person
$550
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Appleton (ATW)
8.8/10 Excellent! (469 reviews)
Really only game in town...they raise prices during events.

Reviewed on Aug 20, 2025

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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
$107 nightly
The price is $124 total per night from Aug 28 to Aug 29
$124 total
Aug 28 - Aug 29
Total with taxes and fees
8.6/10 Excellent! (1,114 reviews)
Beware of the rooms adjacent to housekeeping stora
"We asked for a suite that was not close to the elevator and instead we’re giving a suite where the elevator is actually directly adjacent to the bedroom wall. This was a service elevator and that particular room is next to housekeeping storage. Beginning at 8 AM there is a constant in and out of ..."

Reviewed on Aug 21, 2025

Oneida Casino Hotel
Hyatt Regency Green Bay

Hyatt Regency Green Bay

3.5 out of 5
333 Main St, Green Bay, WI
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $110 total per night from Sep 14 to Sep 15
$110 total
Sep 14 - Sep 15
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Convenient location"

Reviewed on Aug 22, 2025

Hyatt Regency Green Bay
Tundra Lodge

Tundra Lodge

3.5 out of 5
865 Lombardi Ave, Green Bay, WI
$132 nightly
The price is $152 total per night from Sep 17 to Sep 18
$152 total
Sep 17 - Sep 18
Total with taxes and fees
7.4/10 Good! (1,346 reviews)
"Enjoyed it"

Reviewed on Aug 25, 2025

Tundra Lodge
See all 609 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.

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Frequently asked questions

How much does a Pittsfield vacation package cost?
You can pick up a vacation package to this destination from $511 on Expedia. However, how much your vacation to Pittsfield costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
You can usually find reduced prices and greater availability in December, January and February. Browse our cheap Pittsfield vacation packages and you could score some great off-season discounts.
How many days is enough for Pittsfield?
The ideal duration for your Pittsfield vacation depends on what you'd like to do. Usually, a handful of days to a week will give you time to tick off all the leading sights and explore some hidden spots along the way.
How to find the best Pittsfield package deals?
Use Expedia's filter tool to find some terrific 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 trip for midweek, or search for Pittsfield package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your next Pittsfield getaway by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pittsfield?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Pittsfield escape.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield break should be an escape from your busy life, not a reason for money worries. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.