Pittsfield Vacations from $824
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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.
Lake Bomoseen Lodge
$824
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Rutland (RUT)
9.4/10 Exceptional! (985 reviews)
We had a great stay here! This was a long weekend girls' trip. There was easy access to the lake, a clean property, and really good food on-site at the restaurant with live music. The sweet potato hummus is a must-try! The pool was refreshing with plenty of activities to choose from: cornhole, volleyball, and pickleball. There's a little ice cream shop open in the afternoon. You can take a ride on the catamaran or the tiki boat for a small fee. Our stay was reasonably priced. The staff was friendly. Just an easy, no-nonsense, enjoyable getaway. We loved it and are thinking about making this a yearly girls' trip! Thank you so much for a great stay!
Reviewed on Sep 17, 2026
Castle Hill Resort And Spa
$1,101
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9/10 Wonderful! (124 reviews)
We stayed in a two bedroom condo that was fabulous. It was very clean. It had a fireplace and anything we needed was available. One thing that was upsetting is that there was a wedding Saturday night at the castle so we were unable to have dinner there and then they were closed on Sunday so both nights of our stay we could not have dinner at the castle, which we were actually looking forward to. We had a great time regardless of that, we ended up having dinner at Murdock which was sooooo good highly recommend. We didn't use the pool because it was a little chilly, but it looked great. Would go back again especially for ski season.
Reviewed on Sep 15, 2026
The Vermont Inn
$1,075
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9.2/10 Wonderful! (431 reviews)
The place needs a little help. The room was cute but one of the sinks needed cleaning and there was
No coffee creamer and the place needs tlc. A little disappointed but
I get it
Reviewed on Aug 8, 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! (129 reviews)
"Great home for a quiet mountain retreat! The host was very communicative and responsive. Home was very clean, the kitchen had everything you could need as far as cookware and appliances. Great location in Vermont to explore all the state has to offer."
Reviewed on Sep 12, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
$172 total
Oct 18 - Oct 19
Total with taxes and fees
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$739 nightly
$813 total
Sep 20 - Sep 21
Total with taxes and fees
9.4/10 Exceptional! (608 reviews)
"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs ..."
Reviewed on Sep 17, 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 $824 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.
