Pittsfield Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Pittsfield

Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$661 per night from 6 Jul to 7 Jul
S$661
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (519 reviews)
Stunning
"Always a stunning stay in Woodstock!"

Reviewed on 2 Jun, 2025

Woodstock Inn & Resort
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is S$176 per night from 6 Jul to 7 Jul
S$176
6 Jul - 7 Jul
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Good"

Reviewed on 11 Jun, 2025

Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is S$207 per night from 25 Jun to 26 Jun
S$207
25 Jun - 26 Jun
includes taxes & fees
7.2/10 Good! (1,004 reviews)
"The property, rooms and hot tub area's were all clean. The staff there were very polite. We loved our stay and will definitely be back."

Reviewed on 15 Jun, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,737 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.