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Hotels in Pittsfield

Choose from 1833 Pittsfield Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
  • 23 min drive from Pittsfield Town Hall
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.4/10 Good! (1,000 reviews)
"Very nice bed with comfortable mattress"

Reviewed on Jun 9, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
  • 53 min drive from Pittsfield Town Hall
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (583 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Woodstock Inn & Resort
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
  • 44 min drive from Pittsfield Town Hall
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture ...
9.4/10 Exceptional! (461 reviews)
"The room was great. Plenty of space, full size fridge with microwave and toaster. Everything was better than expected."

Reviewed on Jun 5, 2026

My Place Hotel-Randolph VT
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
  • 23 min drive from Pittsfield Town Hall
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,009 reviews)
"Very friendly staff clean room great location and the pool was the best!"

Reviewed on Jun 8, 2026

The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
  • 54 min drive from Pittsfield Town Hall
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (935 reviews)
"It was a very comfortable and nice place to stay with a lot of things within walking distance and having it next to the river was fun. They also have bonfires that you can sit by at night. It was a wonderful day."

Reviewed on Jun 10, 2026

The Shire Woodstock
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
  • 50 min drive from Pittsfield Town Hall
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,003 reviews)
"Great stay. Beautiful location"

Reviewed on Jun 6, 2026

On The River Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
  • 38 min drive from Pittsfield Town Hall
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,003 reviews)
"Horrible dinghy place. Hot tub not working. Room I requested not available."

Reviewed on Jun 3, 2026

Comfort Inn Rutland - Killington
Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd Rutland VT
  • 40 min drive from Pittsfield Town Hall
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,000 reviews)
"Overall, it was a good experience. The room was clean and the bed fairly comfortable. Good breakfast and friendly staff. The location is good and there is plenty of parking."

Reviewed on Jun 7, 2026

Hampton Inn Rutland
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7 Rutland VT
  • 40 min drive from Pittsfield Town Hall
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 ...
6.6/10 (1,006 reviews)
"Could be cleaners in the room. Found hair all over the bathroom."

Reviewed on Jun 9, 2026

Days Inn by Wyndham Rutland/Killington Area
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street Brandon VT
  • 45 min drive from Pittsfield Town Hall
Stay at this hotel in Brandon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (637 reviews)
"Spacious comfortable family suite. Convenient location, clean beautiful inn, great customer service."

Reviewed on May 31, 2026

Brandon Inn
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
  • 17 min drive from Pittsfield Town Hall
Book a stay at this family-friendly hotel in Killington. Enjoy free breakfast, a sauna, and a 24-hour front desk. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (226 reviews)
"Awesome place to stay away from all chaos! The amenities are great but Victoria and Mike are who really made our stay a pleasure. If you’re looking for a laid back but somewhat luxurious place to unwind, this is it!"

Reviewed on Jun 8, 2026

Mountain Meadows Lodge
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
  • 45 min drive from Pittsfield Town Hall
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (581 reviews)
"As a dog owner, this was the perfect stay. It is so convenient to have your car right there. The AC worked VERY well and the room was tidy, beautiful, and well kept. Everything worked great and appreciated the coffee in the morning! Just note you may not have great cell service, so knowing your room ..."

Reviewed on Jun 10, 2026

Sleep Woodstock Motel
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 cheap hotels in Pittsfield

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