Find hotels in Pittsfield, VT from 2.833.001 ₫

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14 Dec - 15 Dec
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15 Dec - 16 Dec
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19 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Pittsfield hotels

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The price is 11.392.509 ₫
25.729.734 ₫ total
includes taxes & fees
16 Dec - 17 Dec
The Getaway 4 Bedroom Home
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1000)
"The staff is wonderful! Friendly, helpful and they work very hard. The room was clean but a little small for our liking so we will make sure to book a larger room next time. You can't beat the location. It's so close to everything!"
United States
Jennifer
The price is 4.711.847 ₫
5.183.032 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Inn & Suites Rutland-Killington
Lobby
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1003)
"Clean, great steak house by the hotel"
United States
Caridad
The price is 3.465.947 ₫
3.812.542 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Comfort Inn Rutland - Killington
Lobby
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.4 out of 10, (1002)
"The food "
United States
Elijah
The price is 3.130.533 ₫
3.443.586 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Days Inn by Wyndham Rutland/Killington Area
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (555)
"Highly recommend stay here"
United States
Margie
The price is 8.918.073 ₫
10.967.388 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (970)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is 3.872.390 ₫
4.259.629 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Rutland
BBQ/picnic Area
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (342)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is 2.684.893 ₫
2.926.533 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
My Place Hotel-Randolph VT
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is 2.154.543 ₫
4.448.250 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Sleep Woodstock Motel
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
Front of property
The Vermont Inn

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415)
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is 6.747.745 ₫
7.355.042 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Vermont Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (179)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is 5.179.848 ₫
6.355.508 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Mountain Meadows Lodge
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (652)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is 2.604.393 ₫
2.864.832 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Cortina Inn
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (959)
"Great place to stay!"
United States
Stephen
The price is 6.132.162 ₫
7.082.897 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The Mountain Inn at Killington
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (397)
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is 4.569.526 ₫
5.026.478 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Summit Lodge
Exterior
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
Killington
7.4 out of 10, Good, (1004)
"Staff was very helpful and room service was great."
United States
Ankita
The price is 5.540.254 ₫
6.094.279 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
Garden
North Star Lodge and Resort

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1001)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Front of property
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (566)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is 3.146.317 ₫
3.460.948 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Brandon Inn
Premium Suite, Multiple Beds | Balcony
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (984)
"Great place, good rates"
United States
Alexander
The price is 3.393.603 ₫
3.732.963 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Sports Inn
The Jewel | Living area | TV
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (96)
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is 8.549.775 ₫
9.319.255 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Mountain Top Inn & Resort
Interior detail
The Trailside Inn

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (134)
"Such a great, comfortable place to stay with an awesome staff!"
United States
Daniel
The price is 4.035.494 ₫
4.439.043 ₫ total
includes taxes & fees
15 Dec - 16 Dec
The Trailside 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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Stay near popular Pittsfield attractions

Roger Clark Memorial Central Library

After visiting Roger Clark Memorial Central Library, make a plan to see the other sights and activities in Pittsfield.
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Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Top Pittsfield Hotel Reviews

Cortina Inn

Cortina Inn

10/10 Excellent
"Warm"
Sarah 1-night trip
Posted 8 days ago
Cortina Inn

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is 2.684.893 ₫ per night from 4 Jan to 5 Jan
2.684.893 ₫
2.926.533 ₫ total
4 Jan - 5 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (342 reviews)

Hotels in Pittsfield with star rating

Frequently asked questions

What's the seasonal weather in Pittsfield?
The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -5°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.

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