Pittsfield Vacations from $573

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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.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $706, price is now $573 per person
$573
per person
Feb 25 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.4/10 Exceptional! (329 reviews)
Had no way of finding out the wifi password until the last day.

Reviewed on Jan 20, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,589, price is now $1,238 per person
$1,238
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $953, price is now $789 per person
$789
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Clean room, great staff-very friendly from front desk to restaurant and hot tub area. Lovely place!! Be aware-they charge to park there, even as a guest at hotel!!!!

Reviewed on Jan 20, 2026

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,311, price is now $1,088 per person
$1,088
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
No reviews
Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,750, price is now $1,498 per person
$1,498
per person
Mar 5 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Rutland (RUT)
No reviews
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Pittsfield Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night from Feb 22 to Feb 23
$384 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (560 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Woodstock Inn & Resort
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
$182 nightly
The price is $200 total per night from Feb 22 to Feb 23
$200 total
Feb 22 - Feb 23
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Solid accommodations.

Reviewed on Jan 12, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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
$140 nightly
The price is $154 total per night from Feb 1 to Feb 2
$154 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (1,006 reviews)
Everything great

Reviewed on Jan 19, 2026

Comfort Inn Rutland - Killington
See all 1,826 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 $573 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.