Find hotels in Pittsfield, VT from 2.833.001 ₫

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15 Dec - 16 Dec
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16 Dec - 17 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
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
16 Dec - 17 Dec
The Mountain Top Inn & Resort
Exterior
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
16 Dec - 17 Dec
Comfort Inn Rutland - Killington
Room, 1 King Bed, Non Smoking | Desk, blackout curtains, iron/ironing board, free cots/infant beds
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 3.108.172 ₫
3.418.989 ₫ total
includes taxes & fees
18 Dec - 19 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
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
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)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is 5.077.251 ₫
6.549.654 ₫ total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
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)
"Beautiful fireplace at the breakfast area in the morning, very helpful staff and quaint hotel."
United States
BETTY
The price is 4.711.847 ₫
5.183.032 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Inn & Suites Rutland-Killington
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 2.036.162 ₫
4.318.031 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Sleep Woodstock Motel
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (544)
"Great hotel, fairly centered , great staff!"
United States
Angelo
The price is 3.051.612 ₫
3.356.773 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
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
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 4.229.113 ₫
4.652.024 ₫ total
includes taxes & fees
14 Jan - 15 Jan 2026
Hampton Inn Rutland
Interior
Lincoln Inn & Gallery

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 3.788.208 ₫
4.167.029 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Lincoln Inn & Gallery
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (653)
"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
16 Dec - 17 Dec
Cortina Inn
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 6.550.443 ₫
7.205.488 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Stay At Jimmy's
Classic Room, 2 Queen Beds | Desk, iron/ironing board, free WiFi, bed sheets
Middlebury Sweets Motel

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (388)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is 2.575.455 ₫
2.833.001 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Middlebury Sweets Motel
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, (48)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
The price is 4.883.105 ₫
5.371.626 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Vesper
Exterior
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
16 Dec - 17 Dec
Brandon Inn
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
16 Dec - 17 Dec
The Vermont 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, (961)
"Great place to stay!"
United States
Stephen
The price is 5.895.399 ₫
6.809.304 ₫ total
includes taxes & fees
21 Dec - 22 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

Cortina Inn

Cortina Inn

10/10 Excellent
"I am so happy with the service "
Sagrario 1-night trip
Posted 4 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 2.635.645 ₫ per night from 1 Jan to 2 Jan
2.635.645 ₫
2.872.853 ₫ total
1 Jan - 2 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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