
Pittsfield Vacations from $679
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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.

The Mountain Inn at Killington
Price was $832, price is now $679 per person
$679
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Rutland (RUT)
9.2/10 Wonderful! (919 reviews)
The staff is super friendly and helpful. Their service is outstanding.
Reviewed on Oct 29, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Price was $1,460, price is now $1,121 per person
$1,121
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!
Reviewed on Nov 5, 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was $2,908, price is now $2,359 per person
$2,359
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
9/10 Wonderful! (51 reviews)
Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention.
Reviewed on Oct 27, 2025

Golden Stage Inn B&B
Price was $1,044, price is now $849 per person
$849
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Miami (MIA) to Rutland (RUT)
10/10 Exceptional! (26 reviews)
If you're looking for a cozy, welcoming, and thoughtfully run bed-and-breakfast, the Golden Stage Inn is a true gem. Julie, Mike, and their sweet dog Maisie have created something special—an atmosphere that feels both homey and quietly luxurious.
Every detail is designed for comfort and delight. The breakfasts are consistently amazing, with fresh, hearty options that start your day off right. Our room was not only beautifully kept but also had its own heat adjustment, which made it easy to stay comfortable no matter the weather. The beds? Exceptionally comfortable. We slept soundly every night thanks to the quiet surroundings and the peaceful energy of the inn.
The amenities go far beyond the basics. There’s free parking, of course, but also a puzzle table, board games, and a living room that feels like the heart of the house—complete with soft seating and a glowing fireplace that makes it the perfect spot to read or unwind. Throughout the day, you’ll find hot apple cider, coffee, tea, and cookie jars filled with fresh-baked cookies that somehow taste like childhood and comfort all at once.
Outside, the charm continues. We loved visiting the chickens and soaking in the views—especially at night. The stargazing here is unmatched. It’s the kind of place where you look up and remember how vast and beautiful the world can be.
We had a wonderful time and can’t recommend the Golden Stage Inn enough. It’s not just a place to stay—it’s a place to feel restored.
Reviewed on Oct 18, 2025

North Star Lodge and Resort
Price was $1,401, price is now $1,159 per person
$1,159
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
8.6/10 Excellent! (1,012 reviews)
Location was great and was clean but the facility and room is old. Needs a major face lift.
Reviewed on Oct 27, 2025
Pittsfield Hotel Deals

Killington Vermont Ski and Snowmobiling House
Pittsfield
9/10 Wonderful! (38 reviews)
Amazing stay!
Was not listed that soaps and toilet paper is not included. Just would’ve preferred that be out in the listing
Reviewed on Mar 13, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
Total with taxes and fees
7.2/10 Good! (1,001 reviews)
Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!
Reviewed on Nov 5, 2025

Comfort Inn Rutland - Killington
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $121 total per night from Nov 9 to Nov 10
$121 total
Nov 9 - Nov 10
Total with taxes and fees
8/10 Very Good! (1,013 reviews)
Quiet and low key.
Reviewed on Nov 2, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















