Pittsfield, VT
Travel Guide
Visit Pittsfield
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (531 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."
Reviewed on Jul 30, 2025
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $218 total per night from Aug 27 to Aug 28
$218 total
Aug 27 - Aug 28
Total includes taxes and fees
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (806 reviews)
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Reviewed on Aug 19, 2025
Days Inn by Wyndham Rutland/Killington Area
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
$101 nightly
The price is $111 total per night from Aug 24 to Aug 25
$111 total
Aug 24 - Aug 25
Total includes taxes and fees
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,005 reviews)
"Clean and comfortable. Good value for what you get. Would stay again."
Reviewed on Aug 18, 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.
Cozy Loft for two with Hot Tub & Mtn Views
Granville
Stay at this cabin in Granville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Plush Quartz Art Glass - Glassblowing Studio & Gallery ...
10/10 Exceptional! (253 reviews)
"Dealing with Jeff was a breeze and the property is awesome! We had a couple of questions that popped up after check in and Jeff was responding to my text message within minutes!The cabin is neat, cozy, and romantic set on a long private driveway with a great deck and hot tub! We found lots of close ..."
Reviewed on Aug 13, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3387 East Mountain Road, Killington, VT
Stay at this 3-star ski cabin in Killington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Killington Resort and Skyeship Express Gondola Stage ...
8.8/10 Excellent! (47 reviews)
"Great value, comfortable space, responsive host!"
Reviewed on Aug 13, 2025
Mountain Green
133 E Mountain Rd Killington, Killington, VT
Stay at this condo in Killington. Enjoy free parking, a picnic area, and an indoor pool. Popular attractions Killington Resort and Black Dog Sports are located ...
6.6/10 (10 reviews)
"The bad reviews must be old. The place was beautiful (bigger than it looked in the pictures too) and the amenities were on point!"
Reviewed on May 6, 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.
Popular places to visit
Roger Clark Memorial Central Library
After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
Pittsfield Town Hall
After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
Explore a world of travel with Expedia
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- Killington Resort
- Middlebury College
- Green Mountain National Forest
- Pico Mountain at Killington Ski Resort
- Killington Peak
- Lake Bomoseen
- Billings Farm and Museum
- Vermont State Fairgrounds
- Paramount Theater
- Wilson Castle
- Killington Adventure Center
- Lake Rescue
- Sunrise Village Triple Ski Lift
- Marsh-Billings-Rockefeller National Historical Park
- Silver Lake State Park
- Moss Glen Falls
- Mad River Valley
- Killington Golf Course
- Saskadena Six Ski Area
- Gifford Woods State Park
- Bear Mountain Quad Ski Lift
- Woodstock Town Hall Theatre
- Sugarbush Farm
- Rutland Regional Medical Center
- Mad River
- Green Mountain National Golf Course
- K-1 Express Gondola
- Woodstock Country Club