A lake surrounded by autumn-colored trees and a rocky shoreline.

Find hotels in Pittsfield, VT from 3.161.965 ₫

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Our top choices for Pittsfield hotels

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,004 reviews)
"Beautiful place to stay"
United States
Jeff
The price is 5.500.671 ₫
6.485.002 ₫ total
includes taxes & fees
21 Jul - 22 Jul
On The River Inn

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (944 reviews)
"It was a very comfortable and nice place to stay with a lot of things within walking distance and having it next to the river was fun. They also have bonfires that you can sit by at night. It was a wonderful day."
United States
Robert
The price is 4.219.346 ₫
5.012.642 ₫ total
includes taxes & fees
8 Jul - 9 Jul
The Shire Woodstock

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (75 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is 4.974.291 ₫
5.471.721 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Lincoln Inn & Gallery

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (64 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is 4.605.825 ₫
5.066.408 ₫ total
includes taxes & fees
28 Jun - 29 Jun
The Vesper

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (288 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is 4.974.291 ₫
5.471.720 ₫ total
includes taxes & fees
25 Jun - 26 Jun
The Jackson

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is 6.553.431 ₫
7.208.774 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Stay At Jimmy's

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (584 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is 2.037.091 ₫
3.161.965 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Sleep Woodstock Motel

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (586 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is 15.238.701 ₫
17.920.607 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Woodstock Inn & Resort

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (2 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is 6.123.116 ₫
6.735.428 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Deer Brook Inn

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (473 reviews)
"Great stay for passing through. It’s super clean and great dog friendly option"
United States
John
The price is 3.012.999 ₫
3.284.169 ₫ total
includes taxes & fees
21 Jul - 22 Jul
My Place Hotel-Randolph VT

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (336 reviews)
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
The price is 6.940.320 ₫
7.634.352 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Kedron Valley Inn

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean, comfortable and great location. Plus they have a hotel dog on staff!"
United States
Laura
The price is 3.292.507 ₫
3.803.095 ₫ total
includes taxes & fees
30 Jun - 1 Jul
The Mountain Inn at Killington

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (4 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is 4.447.016 ₫
4.847.247 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Green Trails Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is 6.066.266 ₫
6.612.230 ₫ total
includes taxes & fees
24 Jun - 25 Jun
Echo Lake Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Great place"
United States
Peter
The price is 2.868.771 ₫
3.155.648 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Mountain Sports Inn

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,002 reviews)
"Another great stay. The hot pool is rad. It is super mega to have the bar and restaurant on-site! Staff are always friendly and helpful."
United States
patrick
The price is 3.256.965 ₫
3.582.662 ₫ total
includes taxes & fees
7 Jul - 8 Jul
North Star Lodge and Resort

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,003 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is 3.293.007 ₫
3.622.308 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Comfort Inn Rutland - Killington

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (231 reviews)
"Beautiful couple for hosts and stunning location. Great breakfast and hot tub to relax after a long drive. Will come back to stay longer"
Canada
Tanuja
The price is 3.914.162 ₫
4.963.501 ₫ total
includes taxes & fees
9 Jul - 10 Jul
Mountain Meadows Lodge

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,000 reviews)
"The staff was amazing!!! We will book this again in our next travels up!"
United States
Carol
The price is 2.998.453 ₫
3.298.298 ₫ total
includes taxes & fees
2 Jul - 3 Jul
Days Inn by Wyndham Rutland/Killington Area

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (189 reviews)
"Location is great"
United States
Lei
The price is 3.632.022 ₫
3.995.224 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Après Inn 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

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

A lake surrounded by autumn-colored trees and a rocky shoreline.

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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.