If you're looking to discover somewhere new, look no further than Pittsfield. Whether you're planning to stay for a night or for the week, the area around Pittsfield has accommodations to fit every need. Search for hotels in Pittsfield with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Pittsfield hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Pittsfield hotel deals are here with our lowest price guarantee.
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Winding Way Chalet 3 Bedroom Home
Winding Way Chalet 3 Bedroom Home
The price is $2,956
includes taxes & fees
$2,688 per night
Jan 2 - Jan 3, 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.
Learn more about Pittsfield
The region around Pittsfield is home to attractions such as Green Mountain National Forest and Pico Mountain at Killington Ski Resort.
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- Hotels near Middlebury College
- Hotels near Killington Peak
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- Hotels near Pico Mountain at Killington Ski Resort
- Hotels near Sunrise Village Triple Ski Lift
- Hotels near Billings Farm and Museum
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- Hotels near Saskadena Six Ski Area
- Hotels near Bear Mountain Quad Ski Lift
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- Grey Bonnet Inn
- The Mountain Top Inn & Resort
- The Trailside Inn
- Mountain Meadows Lodge
- Happy Bear Motel
- Killington Grand Hotel
- Mountain Valley Retreat
- Ski in & out Spruce Glen Townhomes on Great Eastern Trail
- Waybury Inn
- The Lilac Inn
- The Lincoln Inn & Restaurant At The Covered Bridge
- Middlebury Sweets Motel
- Killington Center Inn & Suites by Killington VR - Studios
- Echo Lake Inn
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