Find hotels in Pittsfield, VT from 2.835.585 ₫

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24 Dec - 25 Dec
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25 Dec - 26 Dec
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26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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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 Getaway 4 Bedroom Home
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 Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Terrace/patio
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1002)
"Rearaurant staff was top notch. "
United States
Daniel
The price is 8.557.575 ₫
10.378.891 ₫ total
includes taxes & fees
29 Dec - 30 Dec
On The River Inn
Room 22 | Free WiFi, bed sheets
Kedron Valley Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (329)
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
Kedron Valley Inn
Deluxe Suite | Individually decorated, desk, blackout curtains, iron/ironing board
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 2.059.084 ₫
3.910.680 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Sleep Woodstock Motel
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is 8.399.589 ₫
10.398.112 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (183)
"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
The price is 5.764.294 ₫
6.999.048 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
"Charming bed and breakfast"
United States
Nicholas
The price is 4.887.560 ₫
5.376.527 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
The Vesper
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
The price is 2.896.410 ₫
3.272.943 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Mountain Valley Retreat
Bicycling
Turn of River Lodge

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 3.030.961 ₫
3.334.031 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Turn of River Lodge
Terrace/patio
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, (1002)
"Wonderful experience definitely would stay again."
United States
Ariel
The price is 5.156.001 ₫
5.671.601 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (398)
"The staff was really great and helpful. There are a number of very cool public spaces to enjoy"
United States
George
The price is 4.573.695 ₫
5.031.064 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Summit Lodge
Front of property
Stay At Jimmy's

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 6.556.419 ₫
7.212.062 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Stay At Jimmy's
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
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, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (374)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is 6.216.749 ₫
7.522.240 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Snowed Inn
Lounge
Greenbrier Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (646)
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
Greenbrier Inn
Exterior
Après Inn Killington

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (164)
"Wonderful location, beautiful renovations, friendly staff "
United States
Robyn
The price is 5.087.149 ₫
5.595.864 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
Après Inn Killington
Front of property
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (987)
"Staff was great and breakfast was excellent "
United States
Bruce
The price is 3.396.699 ₫
3.736.369 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Mountain Sports Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is 7.674.433 ₫
8.365.132 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Echo Lake 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

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is 2.666.014 ₫ per night from 18 Jan to 19 Jan
2.666.014 ₫
2.905.955 ₫ total
18 Jan - 19 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (346 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.