Pittsfield Vacations from $503
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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.
The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$503
per person
Oct 29 - Nov 1
found 16 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9/10 Wonderful! (862 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
Mountain Green Resort
$1,499
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Harvest Barn Inn
$652
per person
Oct 15 - Oct 19
found 15 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9.8/10 Exceptional! (274 reviews)
Our stay was absolutely lovely, the owners of this adorable inn are the absolute sweetest couple and incredible cooks! The place is beautifully appointed but what really made the stay extra special was the home cooked, incredible fresh, out of this world breakfast with a stunning view overlooking the river!
10/10 would and will recommend to everyone!
Reviewed on Aug 23, 2026
Lake Bomoseen Lodge
$1,419
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
9.4/10 Exceptional! (972 reviews)
This hotel is right on the lake and we loved the view from our room.Across the street is the grill that has a great variety of food and have an excellent beer selection.The lake is very pretty and the water is clear.
Reviewed on Aug 25, 2026
Stay near popular Pittsfield attractions
Roger Clark Memorial Central Library
After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
Pittsfield Town Hall
After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
Pittsfield Hotel Deals
Killington area home - 4-seasons, hot tub and A/C
Pittsfield VT
9.8/10 Exceptional! (128 reviews)
"House was very nice overall. Spacious and well laid out. Certain things felt a little dirty - grout in the showers, the bedding, etc. Nothing egregious, just not pristinely clean."
Reviewed on Jul 20, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$437 nightly
$481 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (599 reviews)
"Amazing! Will visit again."
Reviewed on Aug 7, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$146 nightly
$161 total
Aug 27 - Aug 28
Total with taxes and fees
9.2/10 Wonderful! (1,031 reviews)
"Such a great experience and stay. We checked in as guests and left as family. The rooms were clean and comfortable, the location perfect, and the staff beyond friendly and helpful. Will definitely be returning."
Reviewed on Aug 25, 2026
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 | Rutland Southern Vermont Regional Airport (RUT) |
Population | 540 |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Center |
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Frequently asked questions
How much does a Pittsfield vacation package cost?
You can snap up a vacation package to this destination from $503 on Expedia. But how much your vacation to Pittsfield costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Pittsfield?
April, May and June are the best times to look for cheap Pittsfield vacation packages. Traveling in quieter periods means you can usually find better prices on accommodations and flights.
How many days is enough for Pittsfield?
The ideal length for your Pittsfield vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to visit all the leading sights and discover some hidden spots 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 vacation package as early as possible.
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 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 vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Pittsfield vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.