Pittsfield hotels from HK$845

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9 Dec - 10 Dec
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10 Dec - 11 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

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Our top choices for Pittsfield hotels

Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is HK$3,304
HK$7,527 total
includes taxes & fees
11 Dec - 12 Dec
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, (1000)
"The staff is wonderful! Friendly, helpful and they work very hard. The room was clean but a little small for our liking so we will make sure to book a larger room next time. You can't beat the location. It's so close to everything!"
United States
Jennifer
The price is HK$1,393
HK$1,532 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Inn & Suites Rutland-Killington
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very good, (1004)
"Clean, great steak house by the hotel"
United States
Caridad
The price is HK$985
HK$1,084 total
includes taxes & fees
11 Dec - 12 Dec
Comfort Inn Rutland - Killington
Desk, blackout curtains, iron/ironing board, free cots/infant beds
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
Rutland
6.4 out of 10, (1001)
"The food "
United States
Elijah
The price is HK$919
HK$1,011 total
includes taxes & fees
14 Dec - 15 Dec
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, (553)
"Highly recommend stay here"
United States
Margie
The price is HK$2,638
HK$3,244 total
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (968)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is HK$1,145
HK$1,260 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Rutland
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, (342)
"Awesome staff and great room with Kitchenette"
United States
Mary
The price is HK$775
HK$845 total
includes taxes & fees
4 Jan - 5 Jan 2026
My Place Hotel-Randolph VT
Individually decorated, desk, blackout curtains, iron/ironing board
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (548)
"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 HK$602
HK$1,277 total
includes taxes & fees
14 Dec - 15 Dec
Sleep Woodstock Motel
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (889)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
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 HK$1,786
HK$1,946 total
includes taxes & fees
11 Dec - 12 Dec
The Vermont Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (178)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is HK$1,327
HK$1,654 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Meadows Lodge
Front of property
Cortina Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (649)
"Front desk man was very helpful. "
United States
Richard
The price is HK$770
HK$847 total
includes taxes & fees
11 Dec - 12 Dec
Cortina 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, (956)
"Great place to stay!"
United States
Stephen
The price is HK$1,113
HK$1,286 total
includes taxes & fees
11 Dec - 12 Dec
The Mountain Inn at Killington
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 HK$1,351
HK$1,487 total
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)
"Staff was very helpful and room service was great."
United States
Ankita
The price is HK$1,270
HK$1,397 total
includes taxes & fees
14 Dec - 15 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Iron/ironing board, free WiFi, bed sheets
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
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (564)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is HK$884
HK$973 total
includes taxes & fees
11 Dec - 12 Dec
Brandon Inn
Front of property
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (980)
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
United States
Bradford
The price is HK$848
HK$933 total
includes taxes & fees
11 Dec - 12 Dec
Mountain Sports Inn
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 HK$2,529
HK$2,756 total
includes taxes & fees
11 Dec - 12 Dec
The Mountain Top Inn & Resort
Property entrance
The Trailside Inn

The Trailside Inn

3.0 star property
North Sherburne
9.0 out of 10, Wonderful, (134)
"Such a great, comfortable place to stay with an awesome staff!"
United States
Daniel
The price is HK$1,148
HK$1,262 total
includes taxes & fees
11 Dec - 12 Dec
The Trailside 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
"After reading reviews I was pleasantly surprised of the high quality of our room. We had a premium king room in the river house. Was large and bathroom was also large with a jacuzzi tub, shared balcony overlooking the river. Walking distance to town, shops and restaurants. Only stayed one night for a wedding in town but overall had a very good experience!"
Jacqueline 1-night trip
Posted 2 days ago
The Shire Woodstock

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is HK$985 per night from 11 Dec to 12 Dec
HK$985
HK$1,084 total
11 Dec - 12 Dec
includes taxes & fees
8/10 Very Good! (1,002 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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