Find hotels in Pittsfield, VT from Rp1.833.783

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22 Dec - 23 Dec
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23 Dec - 24 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 Rp8.297.280
Rp18.014.084 total
includes taxes & fees
25 Dec - 26 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 Rp5.443.750
Rp5.933.688 total
includes taxes & fees
23 Dec - 24 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, (1007)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is Rp2.406.138
Rp2.646.751 total
includes taxes & fees
4 Jan - 5 Jan 2026
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 Rp2.477.325
Rp2.725.057 total
includes taxes & fees
25 Dec - 26 Dec
Days Inn by Wyndham Rutland/Killington Area
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, (1003)
"Great front desk staff. Rooms were very comfortable. "
United States
JERILYN
The price is Rp3.000.093
Rp3.300.103 total
includes taxes & fees
4 Jan - 5 Jan 2026
Best Western Inn & Suites Rutland-Killington
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 Rp6.348.250
Rp7.720.075 total
includes taxes & fees
5 Jan - 6 Jan 2026
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, (1001)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is Rp3.232.750
Rp4.170.248 total
includes taxes & fees
23 Dec - 24 Dec
On The River Inn
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (546)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is Rp1.979.012
Rp2.176.913 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
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 Rp1.386.900
Rp2.572.465 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel
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, (972)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is Rp2.806.630
Rp3.087.292 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Rutland
Front of property
Cortina Inn

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (656)
"Exelent service and everything is clean I feel so good in the cortina hotel "
United States
sagrario
The price is Rp1.993.250
Rp2.192.576 total
includes taxes & fees
23 Dec - 24 Dec
Cortina Inn
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 Rp3.542.625
Rp3.897.055 total
includes taxes & fees
4 Jan - 5 Jan 2026
Lincoln Inn & Gallery
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 Rp4.296.375
Rp4.683.133 total
includes taxes & fees
23 Dec - 24 Dec
The Vermont 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 Rp4.170.750
Rp4.587.824 total
includes taxes & fees
23 Dec - 24 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 Rp1.639.825
Rp1.803.808 total
includes taxes & fees
30 Dec - 31 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, (51)
"Charming bed and breakfast"
United States
Nicholas
The price is Rp2.826.562
Rp3.109.218 total
includes taxes & fees
23 Dec - 24 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 Rp2.003.300
Rp2.203.630 total
includes taxes & fees
23 Dec - 24 Dec
Brandon 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
The price is Rp3.685.000
Rp4.053.500 total
includes taxes & fees
23 Dec - 24 Dec
Kedron Valley 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.
See properties

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

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

10/10 Excellent
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
Wendy 1-night trip
Posted 1 month ago
The Mountain Top Inn & Resort

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is Rp1.682.370 per night from 11 Jan to 12 Jan
Rp1.682.370
Rp1.833.783 total
11 Jan - 12 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (345 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 9.5 mi (15.3 km) from the heart of Pittsfield, Killington Mountain Lodge, Tapestry Collection by Hilton is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Mountain Inn at Killington and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.
If I need to cancel my hotel reservation in Pittsfield, will I receive a refund?
Yes, you'll find most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of check in. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.
What's the best dog-friendly accommodation option in Pittsfield?
Clear River Inn is a top dog-friendly inn, and offers a restaurant and a nightclub for its human guests. See more pet-friendly hotel accommodations in Pittsfield.
What are some accommodation options with pools in Pittsfield?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. Woodstock Inn & Resort and North Star Lodge and Resort are a couple of other choices that feature an on-site pool. View all hotels with pools in Pittsfield.
How is it to stay in Pittsfield?
Visitors can enjoy all that Pittsfield has to offer, including the bars and restaurants. This city also attracts tourists with its welcoming locals. A top sight in the area is Killington Resort. In Pittsfield, there are 42 hotels and other accommodation options to choose from. Find out more about Pittsfield.
What are the top places to visit in Pittsfield?
Favourite places to visit include Green Mountain National Forest, Roger Clark Memorial Central Library and Pittsfield Town Hall. Additionally, you'll find Killington Resort in the area. Take a look at what more there is to see and do in Expedia's Pittsfield guide.
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.