Pittsfield Hotels

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30 Nov - 1 Dec
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1 Dec - 2 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

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Top 10 trending 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
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 star property
Rutland
8.8 out of 10, Excellent, (1001)
"Was very nice the staff especially Jesica in front desk Talk me about alls the restaurants around the area "
United States
SANTIAGO
The price is €153
includes taxes & fees
7 Dec - 8 Dec
Best Western Inn & Suites Rutland-Killington
Room, 1 King Bed, Non Smoking
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
Rutland
6.4 out of 10, (1003)
"I would rate this place as a B hotel. The hotel is over priced. "
Canada
Brett
The price is €112
includes taxes & fees
2 Dec - 3 Dec
Days Inn by Wyndham Rutland/Killington Area
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very good, (1012)
"Clean, great steak house by the hotel"
United States
Caridad
The price is €110
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Rutland - Killington
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Highly recommend stay here"
United States
Margie
The price is €350
includes taxes & fees
1 Dec - 2 Dec
Woodstock Inn & Resort
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (964)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is €128
includes taxes & fees
7 Dec - 8 Dec
Hampton Inn Rutland
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (546)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is €111
includes taxes & fees
1 Dec - 2 Dec
Sleep Woodstock Motel
Full-sized fridge, microwave, stovetop, coffee/tea maker
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (336)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is €94
includes taxes & fees
19 Dec - 20 Dec
My Place Hotel-Randolph VT
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (886)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The price is €112
includes taxes & fees
3 Dec - 4 Dec
The Shire Woodstock
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (176)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is €177
includes taxes & fees
1 Dec - 2 Dec
Mountain Meadows Lodge
Front of property
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 €190
includes taxes & fees
2 Dec - 3 Dec
The Vermont Inn
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 star property
Killington
9.2 out of 10, Wonderful, (949)
"Excellent hotel. "
United States
Kristan
The price is €178
includes taxes & fees
1 Dec - 2 Dec
The Mountain Inn at Killington
Front of property
Cortina Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (645)
"location is excellent. As this is obviously an abandoned Holiday Inn, hopefully it is a renovation in progress."
United States
DICK
The price is €94
includes taxes & fees
1 Dec - 2 Dec
Cortina Inn
Fireplace
Summit Lodge

Summit Lodge

3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is €165
includes taxes & fees
11 Dec - 12 Dec
Summit Lodge
Terrace/patio
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)
"We love it here."
United States
Vanessa L
The price is €139
includes taxes & fees
4 Dec - 5 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (562)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is €113
includes taxes & fees
1 Dec - 2 Dec
Brandon Inn
Standard Room, 2 Double Beds
North Star Lodge and Resort

North Star Lodge and Resort

2.0 star property
Killington
8.6 out of 10, Excellent, (1003)
"Was perfect for our one night stay "
United Kingdom
Ian
North Star Lodge and Resort
Front of property
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (977)
"This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. "
United States
Lana
The price is €94
includes taxes & fees
1 Dec - 2 Dec
Mountain Sports Inn
The Jewel | Living area
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 star property
Chittenden
9.0 out of 10, Wonderful, (95)
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
United States
Wendy
The price is €305
includes taxes & fees
1 Dec - 2 Dec
The Mountain Top Inn & Resort
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1009)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is €256
includes taxes & fees
5 Dec - 6 Dec
On The River 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

Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Very clean room staff very helpful"
Gary 1-night trip
Posted 3 days ago
Courtyard Middlebury

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is €110 per night from 10 Dec to 11 Dec
€110
10 Dec - 11 Dec
includes taxes & fees
8/10 Very Good! (1,008 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Comfort Inn Rutland - Killington and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This holiday home rental outside Pittsfield is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all 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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Comfort Inn Rutland - Killington and The Mountain Inn at Killington 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. 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. You'll also find Gifford Woods State Park and Pico Mountain at Killington Ski 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.

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