Find hotels in Pittsfield, VT from 2.863.804 ₫

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5 Dec - 6 Dec
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6 Dec - 7 Dec
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5 Dec - 7 Dec
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Top 10 Pittsfield hotels and places to stay

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is 11.420.225 ₫
25.792.330 ₫ total
includes taxes & fees
9 Dec - 10 Dec
The Getaway 4 Bedroom Home
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very good, (1002)
"Clean, great steak house by the hotel"
United States
Caridad
The price is 3.070.903 ₫
3.377.993 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Rutland - Killington
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (966)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is 3.776.327 ₫
4.153.959 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Rutland
Exterior
Courtyard Middlebury

Courtyard Middlebury

3.0 star property
Middlebury
8.8 out of 10, Excellent, (543)
"Great hotel, fairly centered , great staff!"
United States
Angelo
The price is 3.059.036 ₫
3.364.941 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (887)
"Wonderful place to stay!"
United States
Robin
The price is 11.293.446 ₫
13.168.091 ₫ total
includes taxes & fees
26 Dec - 27 Dec
The Shire Woodstock
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1000)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is 8.570.575 ₫
10.394.658 ₫ total
includes taxes & fees
24 Dec - 25 Dec
On The River Inn
Deluxe Suite | Individually decorated, desk, blackout curtains, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (547)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is 2.041.115 ₫
4.328.536 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Sleep Woodstock Motel
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (256)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Interior
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2.0 star property
West Woodstock
8.6 out of 10, Excellent, (57)
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is 4.034.763 ₫
4.438.239 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Lincoln Inn & Gallery
Full-sized fridge, microwave, stovetop, coffee/tea maker
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (339)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is 2.627.343 ₫
2.863.804 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
My Place Hotel-Randolph VT
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is 6.566.379 ₫
7.223.016 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Stay At Jimmy's
Terrace/patio
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, (1001)
"It’s a small beautiful cabin like/feel hotel and they have everything you need and most esp a quick drive to Killington resort Their food is also very good and well prepared. "
United States
Cynthia
The price is 3.870.735 ₫
4.257.808 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (46)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
The price is 4.894.985 ₫
5.384.694 ₫ total
includes taxes & fees
8 Dec - 9 Dec
The Vesper
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (553)
"Highly recommend stay here"
United States
Margie
The price is 8.939.769 ₫
10.994.070 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Room 22 | Free WiFi, bed sheets
Kedron Valley Inn

Kedron Valley Inn

3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (326)
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
The price is 5.801.620 ₫
6.381.782 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Kedron Valley Inn
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
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
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (979)
"This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. "
United States
Lana
The price is 2.874.439 ₫
3.161.883 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Mountain Sports Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (178)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is 4.322.207 ₫
5.413.703 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Mountain Meadows Lodge
Bicycling
Turn of River Lodge

Turn of River Lodge

2.5 star property
Killington
8.8 out of 10, Excellent, (270)
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
The price is 3.335.932 ₫
3.669.789 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Turn of River Lodge
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (953)
"Great place to stay!"
United States
Stephen
The price is 3.773.690 ₫
4.358.862 ₫ total
includes taxes & fees
9 Dec - 10 Dec
The Mountain Inn at Killington
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

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is 3.070.903 ₫ per night from 10 Dec to 11 Dec
3.070.903 ₫
3.377.993 ₫ total
10 Dec - 11 Dec
includes taxes & fees
8/10 Very Good! (1,010 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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