Pittsfield Vacations from $513

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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.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $620, price is now $513 per person
$513
per person
May 21 - May 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (1,150 reviews)
Clean room, friendly staff, good breakfast. Always enjoy staying at the Inn. 👍👍

Reviewed on Apr 5, 2026

Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
Price was $1,347, price is now $1,171 per person
$1,171
per person
May 20 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
9/10 Wonderful! (87 reviews)
Will definitely be back!!

Reviewed on Apr 5, 2026

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
Price was $1,038, price is now $905 per person
$905
per person
May 20 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
8/10 Very Good! (1,002 reviews)
Hot tub is great. Breakfast is very good and great variety of food.

Reviewed on Apr 12, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,001, price is now $881 per person
$881
per person
May 20 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
9.2/10 Wonderful! (1,005 reviews)
Always love our stay - dog friendly and people friendly!

Reviewed on Apr 10, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,042, price is now $918 per person
$918
per person
May 20 - May 24
found 17 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Rutland (RUT)
8.6/10 Excellent! (1,004 reviews)
Plenty of space, storage, and nice kitchen. Room and bathroom was clean, bed was comfortable, and the heated pool with a view of the mountain was a huge plus after a long day of skiing

Reviewed on Apr 8, 2026

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Pittsfield Hotel Deals

Killington area home - 4-seasons, hot tub and A/C

Killington area home - 4-seasons, hot tub and A/C

Pittsfield VT
9.8/10 Exceptional! (124 reviews)
the house was great, and we especially enjoyed the pool table, hot tub, fireplace, and dart board. david was an excellent host and his property manager dave bascomb was also fantastic. 6 inches of snow came 2 days later, and our SUV with AWD couldn’t handle the uphill to the house, and we got stuck ...

Reviewed on Feb 22, 2026

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Killington area home - 4-seasons, hot tub and A/C
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
$139 nightly
The price is $152 total per night from Apr 19 to Apr 20
$152 total
Apr 19 - Apr 20
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
it was good

Reviewed on Apr 8, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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 Apr 20 to Apr 21
$384 total
Apr 20 - Apr 21
Total with taxes and fees
9.4/10 Exceptional! (572 reviews)
Wonderful historic property with warm and thoughtful staff. Even though some areas in the lobby were being refurbished, we still enjoyed the experience. Look forward to returning when the huge fireplace in the lobby is back up and operational.

Reviewed on Apr 10, 2026

Woodstock Inn & Resort
See all 1,845 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 $513 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.