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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.


Super 8 by Wyndham Ticonderoga
per person
Aug 2 - Aug 9
found 12 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
8/10 Very Good! (1,005 reviews)
Friendly helpful staff, clean, and great for the price. Next door to McDonald's amd Walmart, short walk to good convenience store. Us Adirondack taxi! $5 to downtown $15 to train station from hotel
Reviewed on Jun 30, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
7.2/10 Good! (1,003 reviews)
Located not very far from the main road, very peaceful. So grateful that they are a pet friendly resort.
Reviewed on Jul 1, 2025


Emrose Luxury Cabins
per person
Aug 29 - Sep 1
found 2 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
9.4/10 Exceptional! (31 reviews)
We stayed here for the weekend for a wedding and it was so comfortable, clean, and quiet since you get your own cabin. We loved it and would definitely come back! The property was also really accommodating to requests and needs in a timely manner
Reviewed on May 16, 2025
Pittsfield Hotel Deals

Comfort Inn Rutland - Killington
19 Allen St, Rutland, VT
$131 nightly
The price is $144 total per night from Jul 6 to Jul 7
$144 total
Jul 6 - Jul 7
Total includes taxes and fees
8/10 Very Good! (1,001 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."
Reviewed on Jun 26, 2025

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$469 nightly
The price is $516 total per night from Jul 6 to Jul 7
$516 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (521 reviews)
"Relaxing"
Reviewed on Jun 25, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from Jul 13 to Jul 14
$152 total
Jul 13 - Jul 14
Total includes taxes and fees
7.2/10 Good! (1,000 reviews)
"Pleasant stay"
Reviewed on Jun 20, 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.