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Hotels in Pittsfield

Choose from 1732 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! (1,007 reviews)
"Proximity to wear i needed to be."

Reviewed on May 18, 2025

Comfort Inn Rutland - Killington
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)
"All was good"

Reviewed on May 13, 2025

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 Roger Clark Memorial Central Library
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. ...
9.2/10 Wonderful! (517 reviews)
"Super weekend- elegant and relaxed."

Reviewed on May 8, 2025

Woodstock Inn & Resort
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! (739 reviews)
"The river view was gorgeous, and the town was beautiful. I highly recommend walking down to Sante for dinner."

Reviewed on May 11, 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! (796 reviews)
"We were very satisfied with the hotel. We were disappointed in the fact that both their restaurant and bar were closed for cleaning which we didn’t find out until we received a welcome text as we were driving to them. That was one of the reasons we stayed there cause we had heard good things about ..."

Reviewed on May 16, 2025

The Mountain Inn at Killington
506 On the River Inn
506 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! (1,006 reviews)
"Play room had fun basketball challenge and arcade games. Also had a playroom for little ones. Restaurant was only open in the evenings Thursday through Sunday. Our room looked out to the grass and river. It would be fun in the summer."

Reviewed on May 19, 2025

506 On the River Inn
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! (1,004 reviews)
"Quiet. Nothing happening"

Reviewed on May 12, 2025

North Star Lodge and Resort
Lincoln Inn & Gallery
Lincoln Inn & Gallery
2709 West Woodstock Rd, Woodstock, VT
  • 48 min drive from Roger Clark Memorial Central Library
Stay at this inn in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Union Arena Community Center and Ottaquechee River are ...
10/10 Exceptional! (6 reviews)
"Super cozy rooms with large comfortable beds, beautiful outdoor area with a fire pit near the river. If you open your windows at night you can hear the river which is lovely. Just a couple minutes drive from Woodstock center"

Reviewed on May 14, 2025

Lincoln Inn & Gallery
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 breakfast (surcharge). Popular attractions Whale Dance Sculpture ...
9.4/10 Exceptional! (198 reviews)
"Very comfortable and quiet."

Reviewed on May 18, 2025

My Place Hotel-Randolph VT
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! (484 reviews)
Sleep Woodstock Motel getaway
"Very good and clean accomodations in a good location away from downtown. Everything we needed was in the room"

Reviewed on Apr 19, 2025

Sleep Woodstock Motel
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 (1,007 reviews)
"Needs some cleaning up outside."

Reviewed on May 9, 2025

Days Inn by Wyndham Rutland/Killington Area
Hampton Inn Rutland
Hampton Inn Rutland
2.5 out of 5
47 Farrell Rd, 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 breakfast and the helpful staff ...
9/10 Wonderful! (916 reviews)
"Easy check in, close to everything, clean, large room, pet friendly, friendly staff…We’ve stayed here a few times, and it’s very nice! Room rates are reasonable too!"

Reviewed on May 12, 2025

Hampton Inn Rutland
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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