Pittsfield Hotels

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Check prices for these dates

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1 Mar - 2 Mar
Tomorrow
2 Mar - 3 Mar
Next weekend
6 Mar - 8 Mar
In two weeks
13 Mar - 15 Mar

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Our top choices for Pittsfield hotels

Exterior detail

Killington Haus

Killington Haus
2.0 star property
Killington
8.4 out of 10, Very good, (18 reviews)
"Great location to ski resort and excellent Ramen restaurant on site "
United States
Kim
The price is €164
includes taxes & fees
2 Mar - 3 Mar
Killington Haus
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, (108 reviews)
"Great resort "
United States
Adam
The price is €240
includes taxes & fees
2 Mar - 3 Mar
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)
"great hotel"
United States
Shweta
The price is €123
includes taxes & fees
22 Mar - 23 Mar
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, (1,002 reviews)
"Had a great stay"
United States
Jeff
The price is €98
includes taxes & fees
8 Mar - 9 Mar
Days Inn by Wyndham Rutland/Killington Area
Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (565 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is €325
includes taxes & fees
22 Mar - 23 Mar
Woodstock Inn & Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,001 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
On The River Inn
Iron/ironing board, free WiFi, bed sheets

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (914 reviews)
"Wonderful place to stay!"
United States
Robin
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, (1,002 reviews)
"Very good place to stay "
United States
Barbara
The price is €122
includes taxes & fees
2 Mar - 3 Mar
Best Western Inn & Suites Rutland-Killington
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (557 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 €128
includes taxes & fees
2 Mar - 3 Mar
Sleep Woodstock Motel
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (559 reviews)
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is €133
includes taxes & fees
16 Mar - 17 Mar
Courtyard Middlebury
Lobby sitting area

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (63 reviews)
"The accommodations are perfect for a weekend away and less than a 20 minute drive to Killington resort!! It is a very warm and cute stay"
United States
Ronda
The price is €134
includes taxes & fees
2 Mar - 3 Mar
Lincoln Inn & Gallery
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,000 reviews)
"Room was very clean. Staff was very kind, professional. Will most likely stay here again."
United States
Bob
The price is €129
includes taxes & fees
24 Mar - 25 Mar
Hampton Inn Rutland
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (271 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

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (392 reviews)
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is €112
includes taxes & fees
2 Mar - 3 Mar
Middlebury Sweets Motel
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is €278
includes taxes & fees
3 Mar - 4 Mar
Stay At Jimmy's
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is €173
includes taxes & fees
2 Mar - 3 Mar
The Vesper
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (594 reviews)
"Beautiful and unique space, perfect for a weekend getaway in Vermont! "
United States
Sarah
The price is €111
includes taxes & fees
2 Mar - 3 Mar
Brandon Inn
Front of property

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.4 out of 10, (697 reviews)
"Very quiet and comfortable stay."
United States
James
The price is €111
includes taxes & fees
2 Mar - 3 Mar
Cortina Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (424 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 €201
includes taxes & fees
2 Mar - 3 Mar
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, (1,000 reviews)
"Clean room, friendly staff, great location "
United States
Viktor
The price is €149
includes taxes & fees
1 Apr - 2 Apr
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

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
See properties

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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Top Pittsfield Hotel Reviews

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Clean room, staff were super friendly and made sure me and my dog were comfortable. Love how dog friendly it was. Will definitely return!"
Paola 3-night trip
Posted 1 day ago
Killington Mountain Lodge, Tapestry Collection by Hilton

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is €93 per night from 23 Mar to 24 Mar
€93
23 Mar - 24 Mar
includes taxes & fees
9.4/10 Exceptional! (397 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 My Place Hotel-Randolph VT. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Roundabout Ridge: This holiday home rental outside of Pittsfield is located in the mountains, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. 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?
Comfort Inn Rutland - Killington: Offers continental, an indoor pool and free self parking. Best Western Inn & Suites Rutland-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. In Pittsfield, there are 41 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, Pittsfield Town Hall and Roger Clark Memorial Central Library. 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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