Pittsfield Vacations from $834

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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 $983, price is now $834 per person
$834
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
6.4/10 (1,000 reviews)
Staff was good, breakfast was good, room needed paint and cleaning.

Reviewed on Nov 20, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,042, price is now $845 per person
$845
per person
Feb 12 - Feb 16
found 3 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
9/10 Wonderful! (774 reviews)
Very welcoming, spacious, clean. Perfect for a family of 4.

Reviewed on Nov 18, 2025

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,122, price is now $928 per person
$928
per person
Feb 16 - Feb 19
found 21 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
Great place to stay!

Reviewed on Dec 2, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,176, price is now $1,008 per person
$1,008
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews
Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,592, price is now $1,377 per person
$1,377
per person
Jan 23 - Jan 25
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) 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
$379 nightly
The price is $417 total per night from Dec 16 to Dec 17
$417 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 2025

Woodstock Inn & Resort
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
$167 nightly
The price is $184 total per night from Dec 9 to Dec 10
$184 total
Dec 9 - Dec 10
Total with taxes and fees
9/10 Wonderful! (953 reviews)
Nice amenities, clean room, welcoming staff. Only 2 min drive from the Snowshed lodge. The on-site brewery and restaurant are pretty great.

Reviewed on Dec 4, 2025

The Mountain Inn at 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
$167 nightly
The price is $184 total per night from Dec 14 to Dec 15
$184 total
Dec 14 - Dec 15
Total with taxes and fees
7.2/10 Good! (1,000 reviews)
If you want to travel to Killington with your pup, this is a great spot to stay! Right next to a golf course and other open space for dogs to run. Super friendly staff (Tahoe got lots of treats from the front desk). Great location. Good breakfast. Nice outdoor hot tub for a soak after hitting the ...

Reviewed on Dec 1, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
See all 1,787 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 $834 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.