Pittsfield Vacations from $798

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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.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $1,016, price is now $798 per person
$798
per person
Dec 25 - Dec 31
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
7/10 Good! (1,003 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $3,576, price is now $2,620 per person
$2,620
per person
Dec 25 - Dec 31
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
No reviews

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,299, price is now $1,713 per person
$1,713
per person
Jan 14 - Jan 17
found 19 hours ago
Roundtrip non-stop flight included
Greenville (GSP) 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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,205, price is now $922 per person
$922
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
9/10 Wonderful! (890 reviews)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $3,808, price is now $3,071 per person
$3,071
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9/10 Wonderful! (70 reviews)
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.

Reviewed on Oct 15, 2026

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Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Pittsfield Hotel Deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Fully refundable
$125 nightly
The price is $138 total per night from Nov 11 to Nov 12
$138 total
Nov 11 - Nov 12
Total with taxes and fees
Comfort Inn Rutland - Killington
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Nov 5 to Nov 6
$172 total
Nov 5 - Nov 6
Total with taxes and fees
The Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."

Reviewed on Oct 28, 2026

Woodstock Inn & Resort
See all 1,850 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.

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 $798 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.