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Hotels in Pittsfield

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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 ...
8/10 Very Good! (1,011 reviews)
Its good for the price

Reviewed on Feb 20, 2026

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 Pittsfield Town Hall
Book a stay at this 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 clean ...
7.4/10 Good! (1,007 reviews)
Clean and comfortable room, helpful staff, decent breakfast!

Reviewed on Feb 23, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
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! (394 reviews)
Why say kitchenette when you had to purchase all cookwares! Yes pots pans utensils all of it!

Reviewed on Feb 21, 2026

My Place Hotel-Randolph VT
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
  • 30 min drive from Pittsfield Town Hall
Book a stay at this ski hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,006 reviews)
Our stay was delightful, with fresh cookies at check-in, friendly staff, spacious room and amenities, the grounds are well kept and operated with a family owned feel. Killington is 20 min away by major road. Great stay!

Reviewed on Feb 22, 2026

Best Western Inn & Suites Rutland-Killington
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. ...
9.2/10 Wonderful! (565 reviews)
Very clean, high end, friendly staff

Reviewed on Feb 20, 2026

Woodstock Inn & Resort
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
  • 19 min drive from Pittsfield Town Hall
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 ...
8.6/10 Excellent! (1,008 reviews)
Good vibe hotel with heated pool! But room average, cleaness average, staff nice, good location.

Reviewed on Feb 22, 2026

North Star Lodge and Resort
Summit Lodge

Summit Lodge

3 out of 5
200 Summit Road Killington VT
  • 20 min drive from Pittsfield Town Hall
Stay at this inn in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington ...
8.6/10 Excellent! (440 reviews)
Great breakfast and great staff

Reviewed on Feb 22, 2026

Summit Lodge
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
195 Mountain Top Road Chittenden VT
  • 22 min drive from Pittsfield Town Hall
Book a stay at this beach resort in Chittenden. Enjoy an outdoor pool, a private beach, and breakfast (surcharge). Popular attractions Lefferts Pond and Proctor-Pittsford ...
9/10 Wonderful! (107 reviews)
Love this gem of a place! Cozy, great food and yummy cocktails. Exceeded our expectations and the waitstaff was phenomenal-shout out to Brendan the bartender he was awesome Sledding, horse ride in a carriage, skating hot tub and so much more!

Reviewed on Feb 21, 2026

The Mountain Top Inn & Resort
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 ...
6.4/10 (1,002 reviews)
The first room we checked into had dead bugs on the sheets. They switched us to a clean room, but it was disconcerting. The mattress was the least comfortable mattress I have slept on in years. We arrived late (~1am), and had to ring a doorbell while waiting in the cold for desk service. I am familiar ...

Reviewed on Feb 14, 2026

Days Inn by Wyndham Rutland/Killington Area
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! (1,002 reviews)
Pool and sauna were wonderful after a day of skiing. Excellent breakfast.

Reviewed on Feb 14, 2026

On The River Inn
Turn of River Lodge

Turn of River Lodge

2.5 out of 5
5672 US Route 4 Killington VT
  • 23 min drive from Pittsfield Town Hall
Stay at this lodge in Killington. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (283 reviews)
Clean as a whistle

Reviewed on Feb 11, 2026

Turn of River Lodge
Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
  • 19 min drive from Pittsfield Town Hall
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 ...
8.8/10 Excellent! (1,001 reviews)
We had the premium suite. Suited our GM family of 5 just fine. The hotel is a typical mountain side hotel. We booked late and options were limited. We were happy with the room overall.

Reviewed on Feb 16, 2026

Mountain Sports Inn
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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