Pittsfield Vacation Packages

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Your Pittsfield Vacation

Get ready to experience Pittsfield in your own style with a custom Pittsfield vacation package! Uncovering the charms of this captivating city is made easier with a base in a neighborhood such as West Bridgewater, which is good for skiing, among many other things. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just some of the many sights you'll want to see during your trip to Pittsfield. A couple of quick clicks is all it takes to put together your perfect Pittsfield vacation on Expedia.

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Pittsfield Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $563 per night from Sep 1 to Sep 2
CA $563
CA $680 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (530 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul. 30, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
The price is CA $192 per night from Aug 24 to Aug 25
CA $192
CA $224 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (793 reviews)
"Beautiful pet friendly place in the heart of Woodstock Village. Scenery is lovely, soothing and plenty to do. Can walk to things, bike or hike."

Reviewed on Aug. 1, 2025

The Shire Woodstock
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Aug 10 to Aug 11
CA $139
CA $153 total
Aug 10 - Aug 11
includes taxes & fees
6.2/10 (1,000 reviews)
"The room was clean and staff was nice. The lighting was terrible. 3 lights in the room and with all three on, we had to use our cell phone flashlight to read, find things etc. Breakfast was ok but ended up eating at Dennys next door."

Reviewed on Jul. 28, 2025

Days Inn by Wyndham Rutland/Killington Area
See all 1,744 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'll find cheap prices on Expedia for your Pittsfield getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Pittsfield costs.
What are the cheapest months to go to Pittsfield?
To score cheap Pittsfield vacation packages, organize your trip outside of peak periods like public holidays and major events. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Pittsfield?
With a well-planned schedule, you can easily tick off the main Pittsfield sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Pittsfield vacation for longer.
How to find the best Pittsfield package deals?
Start your search for a Pittsfield package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Pittsfield package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pittsfield adventure underway.
Is it cheaper to book a Pittsfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy 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?
If you have your Pittsfield travel dates confirmed, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Pittsfield?

  1. Choose when to get away: Check your calendar and pack your bags. Your favourite season and the type of activities on offer will also help you decide when to visit Pittsfield.
  2. Plan your budget wisely: Besides the cost of your accommodations, you'll need to consider other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could arise during your trip to Pittsfield.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Pittsfield. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've settled on your 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.