Pittsfield Vacation Packages

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Top Pittsfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cobblestone Hotel & Suites - Two Rivers

Cobblestone Hotel & Suites - Two Rivers

3 out of 5
per person
Oct 11 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Green Bay (GRB)
8.6/10 Excellent! (682 reviews)
Clean. Excellent location.

Reviewed on Aug. 3, 2025

Best Western Plus Appleton Airport/Mall Hotel

Best Western Plus Appleton Airport/Mall Hotel

2.5 out of 5
per person
Oct 11 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Appleton (ATW)
8.4/10 Very Good! (1,001 reviews)
Booked for EAA. Room was not cleaned the whole of our 6 day stay but we did get clean towels when we asked. The breakfast was pretty basic and by the last day of our stay the choice was very limited as they said they had run out of food! I feel the hotel was very overpriced for what it was, but this will have been due to the heavy demand for accommodation during Oshkosh. It may be better at other times of the year.

Reviewed on Jul. 27, 2025

DoubleTree by Hilton Neenah

DoubleTree by Hilton Neenah

4 out of 5
per person
Oct 11 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Appleton (ATW)
8.6/10 Excellent! (940 reviews)
A very enjoyable stay. Excellent staff.

Reviewed on Jul. 31, 2025

at the Waters Edge Bed & Breakfast

at the Waters Edge Bed & Breakfast

3 out of 5
per person
Oct 11 - Oct 13
found 19 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Green Bay (GRB)
9/10 Wonderful! (196 reviews)
Kari and Dave are great proprietors. Area is fun to visit.

Reviewed on Jul. 22, 2025

Quality Inn Appleton West

Quality Inn Appleton West

2.5 out of 5
per person
Oct 11 - Oct 13
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Appleton (ATW)
7/10 Good! (694 reviews)
It’s a Quality Inn.

Reviewed on Jul. 23, 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
The price is CA $160 per night from Sep 3 to Sep 4
CA $160
CA $185 total
Sep 3 - Sep 4
includes taxes & fees
8.6/10 Excellent! (1,074 reviews)
"Very quiet and safe location. Close to shopping as well. Great dining options and casino is attached."

Reviewed on Jul. 29, 2025

Oneida Casino Hotel
Tundra Lodge

Tundra Lodge

3.5 out of 5
865 Lombardi Ave, Green Bay, WI
The price is CA $201 per night from Aug 19 to Aug 20
CA $201
CA $270 total
Aug 19 - Aug 20
includes taxes & fees
7.4/10 Good! (1,324 reviews)
"We had a great time at the water park. Most of the staff was really nice, however, there was one front desk lady that was sort of rude and came off short and inconvenienced. The fact that you don't get fresh towels, wash cloths, toilet paper, Kleenex, garbage bags, etc. unless you go ask for it at ..."

Reviewed on Aug. 1, 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 $98 per night from Sep 1 to Sep 2
CA $98
CA $113 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (1,139 reviews)
"Property centrally located. Nice pool but on the smaller side. Excellent breakfast"

Reviewed on Jul. 31, 2025

Hotel J Green Bay
See all 611 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 grab a vacation package to this popular destination from CA $935 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.