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Hotels in Pittsfield

Choose from 1739 Pittsfield Hotel Deals

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
  • 38 min drive from Roger Clark Memorial Central Library
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 ...
8/10 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

Comfort Inn Rutland - Killington
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
  • 53 min drive from Roger Clark Memorial Central Library
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! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on Jun 20, 2025

Woodstock Inn & Resort
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 Roger Clark Memorial Central Library
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.2/10 Good! (1,001 reviews)
"Pleasant stay"

Reviewed on Jun 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
North Star Lodge and Resort
North Star Lodge and Resort
2 out of 5
78 Weathervane Dr, Killington, VT
  • 20 min drive from Roger Clark Memorial Central Library
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.4/10 Very Good! (1,000 reviews)
"The staff made check in a breeze. The king room is large, clean and comfortable. The extra convenience is the restaurant right next door!"

Reviewed on Jun 21, 2025

North Star Lodge and Resort
Cortina Inn
Cortina Inn
3 out of 5
476 Holiday Drive, Rutland, VT
  • 40 min drive from Roger Clark Memorial Central Library
Stay at this 3-star business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping ...
6.8/10 (561 reviews)
"Staff were extremely helpful all during my stay."

Reviewed on Jun 16, 2025

Cortina Inn
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
  • 54 min drive from Roger Clark Memorial Central Library
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! (761 reviews)
"Great location!! Very accommodating and clean."

Reviewed on Jun 28, 2025

The Shire Woodstock
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 out of 5
47 Old Mill Rd, Killington, VT
  • 24 min drive from Roger Clark Memorial Central Library
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. ...
9/10 Wonderful! (816 reviews)
"Was great 👍"

Reviewed on Jun 26, 2025

The Mountain Inn at Killington
My Place Hotel-Randolph VT
My Place Hotel-Randolph VT
2 out of 5
2440 Vermont 66, Randolph Center, VT
  • 43 min drive from Roger Clark Memorial Central Library
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! (213 reviews)
"I was alone and it was 9 degrees and I couldn't sleep in my car. The property was spectacular. will recommend always."

Reviewed on Jun 25, 2025

My Place Hotel-Randolph VT
Days Inn by Wyndham Rutland/Killington Area
Days Inn by Wyndham Rutland/Killington Area
2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
  • 40 min drive from Roger Clark Memorial Central Library
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 (1,004 reviews)
"We love the new renovations. Good job!"

Reviewed on Jun 20, 2025

Days Inn by Wyndham Rutland/Killington Area
Mountain Sports Inn
Mountain Sports Inn
2 out of 5
813 Killington Road, Killington, VT
  • 19 min drive from Roger Clark Memorial Central Library
Stay at this hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (896 reviews)
"The property looks a little worn but we were given a quiet room in the back as requested and the staff was friendly"

Reviewed on Jun 23, 2025

Mountain Sports Inn
On The River Inn
On The River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
  • 50 min drive from Roger Clark Memorial Central Library
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,005 reviews)
"Clean comfortable room. Views are beautiful. Very peaceful sitting on the balcony and relaxing. Breakfast is standard but good. Had dinner at the restaurant our first night and the food was wonderful. Would absolutely recommend staying here."

Reviewed on Jun 23, 2025

On The River Inn
Sleep Woodstock Motel
Sleep Woodstock Motel
2 out of 5
4324 West Woodstock Road, Woodstock, VT
  • 45 min drive from Roger Clark Memorial Central Library
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! (494 reviews)
"This stay was incredibly comfortable. The room was homey and inviting. Newer amenities- very clean. Room had space and was nicely set up. Would stay here again! Very close to great food options (within 20 minutes)."

Reviewed on Jun 27, 2025

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.

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