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Check prices for these dates

Tonight
17 Jan - 18 Jan
Tomorrow
18 Jan - 19 Jan
Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb

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Our top choices for Pittsfield hotels

House, 4 Bedrooms | Exterior

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The Getaway 4 Bedroom Home
Exterior detail

Killington Haus

Killington Haus
2.0 star property
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Very clean, nature oriented furniture, pleasant place. Highly recommended. "
United States
Fellanza
The price is ฿14,067
฿15,474 total
includes taxes & fees
18 Jan - 19 Jan
Killington Haus
The Jewel | Living area | TV

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (101 reviews)
"Room was comfy and clean. The view from the window was gorgeous. The whole resort was so quaint, warm and beautiful. "
United States
Ping
The price is ฿8,165
฿8,899 total
includes taxes & fees
20 Jan - 21 Jan
The Mountain Top Inn & Resort
Lobby

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,003 reviews)
"Rooms were clean and comfortable.."
United States
Nimisha
The price is ฿4,412
฿4,853 total
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn Rutland - Killington
Lobby

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.4 out of 10, (1,001 reviews)
"Had a great stay"
United States
Jeff
The price is ฿4,644
฿5,109 total
includes taxes & fees
22 Jan - 23 Jan
Days Inn by Wyndham Rutland/Killington Area
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (560 reviews)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is ฿10,034
฿12,422 total
includes taxes & fees
19 Jan - 20 Jan
Woodstock Inn & Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"Brilliant stay"
United States
Enrico
The price is ฿7,455
฿9,354 total
includes taxes & fees
12 Feb - 13 Feb
On The River Inn
Property grounds

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (906 reviews)
"Wonderful place to stay!"
United States
Robin
The price is ฿3,914
฿4,650 total
includes taxes & fees
25 Jan - 26 Jan
The Shire Woodstock
Lobby

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"Very easy to get to, very clean and spacious room and excellent staff attention"
United States
Richard
The price is ฿5,624
฿6,187 total
includes taxes & fees
25 Jan - 26 Jan
Best Western Inn & Suites Rutland-Killington
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (555 reviews)
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
The price is ฿2,293
฿4,488 total
includes taxes & fees
19 Jan - 20 Jan
Sleep Woodstock Motel
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (551 reviews)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is ฿3,716
฿4,088 total
includes taxes & fees
25 Jan - 26 Jan
Courtyard Middlebury
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 reviews)
"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
Lobby sitting area

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (59 reviews)
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is ฿3,963
฿4,360 total
includes taxes & fees
19 Jan - 20 Jan
Lincoln Inn & Gallery
Exterior

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (987 reviews)
"Room was very clean. Staff was very kind, professional. Will most likely stay here again."
United States
Bob
The price is ฿4,891
฿5,380 total
includes taxes & fees
8 Feb - 9 Feb
Hampton Inn Rutland
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46 reviews)
"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 ฿7,819
฿8,601 total
includes taxes & fees
26 Jan - 27 Jan
Stay At Jimmy's
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (389 reviews)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is ฿3,074
฿3,382 total
includes taxes & fees
20 Jan - 21 Jan
Middlebury Sweets Motel
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ฿5,829
฿6,412 total
includes taxes & fees
25 Jan - 26 Jan
The Vesper
Front of property

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (674 reviews)
"Very quiet and comfortable stay."
United States
James
The price is ฿3,109
฿3,420 total
includes taxes & fees
15 Feb - 16 Feb
Cortina Inn
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (576 reviews)
"Clean room and staff was wonderful upon check in "
United States
Kaitlyn
The price is ฿3,756
฿4,131 total
includes taxes & fees
20 Jan - 21 Jan
Brandon Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (415 reviews)
"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 ฿8,055
฿8,780 total
includes taxes & fees
19 Jan - 20 Jan
The Vermont 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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Beautiful area. The ground floor room was perfect!"
Andrea 3-night trip
Posted 4 days ago
The Shire Woodstock

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ฿3,083 per night from 8 Feb to 9 Feb
฿3,083
฿3,360 total
8 Feb - 9 Feb
includes taxes & fees
9.2/10 Wonderful! (364 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Killington Mountain Lodge, Tapestry Collection by Hilton and The Mountain Inn at Killington. 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?
Comfort Inn Rutland - Killington: Offers continental, an indoor pool and free self parking. The Mountain Inn at Killington and Woodstock Inn & 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 40 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.