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Hotels in Pittsfield

Choose from 1819 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)
Great location, hot tub and lobby area. Only thing that would make it better is complimentary breakfast and not charging for parking.

Reviewed on Mar 15, 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! (407 reviews)
It was pretty good all around.

Reviewed on Mar 15, 2026

My Place Hotel-Randolph VT
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! (1,004 reviews)
Not much like, everything is old.

Reviewed on Mar 17, 2026

Comfort Inn 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! (567 reviews)
Amazing restaurant and attentive staff

Reviewed on Mar 4, 2026

Woodstock Inn & Resort
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
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
*

Reviewed on Mar 15, 2026

Best Western Inn & Suites Rutland-Killington
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! (1,005 reviews)
Incredibly helpful staff. heated pool was like a hot tub would stay here again

Reviewed on Mar 17, 2026

North Star Lodge and 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 (1,003 reviews)
Great management, super clean, beautiful pool, free onsite parking. Free breakfast.

Reviewed on Mar 13, 2026

Days Inn by Wyndham Rutland/Killington Area
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 ...
8.8/10 Excellent! (450 reviews)
We had a horrible stay and will not stay at this hotel again. This hotel has a lot of problems. The temperature in the room was so hot and the thermostat did not work. I ended up having to open the window and the door to cool the room down. The hot water took over 10 minutes to warm up. On our second ...

Reviewed on Mar 12, 2026

Summit Lodge
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. ...
The Mountain Inn at Killington
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)
Had a lovely stay while visiting, enjoyed the breakfast and the staff were all very friendly and accommodating. Would def stay here again

Reviewed on Mar 16, 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! (287 reviews)
Considering this was a lodge atmosphere with shared amenities, the space was clean, in good operating condition, and provided a friendly atmosphere. The staff worked extremely hard to accommodate the patrons!

Reviewed on Mar 14, 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! (1,003 reviews)
It was great

Reviewed on Mar 14, 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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