Pittsfield Vacations from $484

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

The Latest Pittsfield vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Appleton by IHG

Holiday Inn Appleton by IHG

3 out of 5
Price was $541, price is now $484 per person
$484
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Appleton (ATW)
9.2/10 Wonderful! (477 reviews)
Yes staff was good Breakfast fast not good paid 40 on line for just pancakes and French toast

Reviewed on Nov 16, 2025

Four Points by Sheraton Appleton

Four Points by Sheraton Appleton

3 out of 5
Price was $592, price is now $491 per person
$491
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Appleton (ATW)
8.6/10 Excellent! (1,000 reviews)
Room was very clean, staff was really helpful. Great stay!

Reviewed on Nov 16, 2025

SpringHill Suites Green Bay

SpringHill Suites Green Bay

3.5 out of 5
Price was $1,135, price is now $946 per person
$946
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Green Bay (GRB)
9.2/10 Wonderful! (1,002 reviews)
We enjoyed our stay. Would stay there again

Reviewed on Nov 20, 2025

Fairfield Inn & Suites by Marriott Appleton

Fairfield Inn & Suites by Marriott Appleton

3.5 out of 5
Price was $790, price is now $678 per person
$678
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Appleton (ATW)
9.6/10 Exceptional! (225 reviews)
Clean as a whistle. Nice bed. Hot shower out of the faucet. Roomy. Comfortable. Hot breakfast. Good coffee. Quite jazzed. Usually a fan of a different chain. Impressive Marriott.

Reviewed on Nov 30, 2025

Holiday Inn Express & Suites Green Bay East by IHG

Holiday Inn Express & Suites Green Bay East by IHG

2.5 out of 5
Price was $973, price is now $874 per person
$874
per person
Jan 9 - Jan 12
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Green Bay (GRB)
9.2/10 Wonderful! (1,000 reviews)
Except the shower door did not stay closed and water was everywhere when trying to take a shower. Huge liability and very dangerous. Its interesting because the floor by the refrigerator slopes and is not level which must continue to the shower behind that wall. We liked the size of the room though.

Reviewed on Nov 25, 2025

Don't see what you're looking for?
See all available trips from Columbus to Pittsfield
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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 Dec 3 to Dec 4
$124 total
Dec 3 - Dec 4
Total with taxes and fees
8.6/10 Excellent! (1,302 reviews)
I’m a

Reviewed on Nov 26, 2025

Oneida Casino Hotel
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
$59 nightly
The price is $69 total per night from Dec 3 to Dec 4
$69 total
Dec 3 - Dec 4
Total with taxes and fees
9/10 Wonderful! (1,290 reviews)
Ok

Reviewed on Nov 25, 2025

Hotel J Green Bay
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
$107 nightly
The price is $124 total per night from Dec 4 to Dec 5
$124 total
Dec 4 - Dec 5
Total with taxes and fees
8.6/10 Excellent! (1,016 reviews)
Great staff. Clean room and nice amenities

Reviewed on Nov 23, 2025

Hyatt Regency Green Bay
See all 628 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
Closest Airport
Appleton Intl. Airport (ATW)
Population
2,700

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Pittsfield vacation package cost?
You can pick up a vacation package to this destination from $484 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.