Pittsfield Holidays

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Your Pittsfield Holiday

With everything planned before you take off, our Pittsfield holiday packages mean you can simply focus on enjoying your getaway. Whether you're going to be based in the neighbourhood of West Bridgewater, which is good for skiing, or somewhere else in town, this lively city promises an array of discoveries. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just some of the many attractions worth exploring during your trip to Pittsfield. Whatever your travel plans or budget, organising a tailored Pittsfield holiday is easy with Expedia.

Pittsfield Holiday

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
540
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Centre

Our pick of the best Pittsfield Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$744 per night from 1 Sept to 2 Sept
AU$744
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (532 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 30 Jul. 2025

Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
9/10 Wonderful! (875 reviews)
"The staff was friendly and helpful. We liked the dog behind the front desk."

Reviewed on 24 Aug. 2025

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The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
8.6/10 Excellent! (809 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on 21 Aug. 2025

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The Shire Woodstock
See all 1,734 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Pittsfield holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Pittsfield costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Pittsfield?
Travel in the off-peak season and you're likely to get cheap Pittsfield holiday packages. Remember that public holidays and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Pittsfield?
The ideal duration for your Pittsfield holiday depends on what you'd like to do. Usually, a few days to a week will give you enough time to go to all the major sights and discover some hidden treasures along the way.
How to find the best Pittsfield package deals?
Use Expedia's handy filters to find some great Pittsfield package deals. When you begin your search, just 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. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Pittsfield holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the freedom to create a tailored Pittsfield holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Pittsfield?
If you have your Pittsfield travel dates finalized, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Pittsfield?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Pittsfield.
  2. Budget wisely: On top of the price of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Pittsfield.
  3. Determine how many days away: Start by compiling a list of the activities and sights you want to get to in Pittsfield. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Pittsfield holiday package.

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