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7 Feb - 8 Feb
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8 Feb - 9 Feb
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13 Feb - 15 Feb
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20 Feb - 22 Feb

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Our top choices for Pittsfield hotels

Exterior detail

Killington Haus

Killington Haus
2.0 star property
Killington
8.8 out of 10, Excellent, (10 reviews)
"Great location to ski resort and excellent Ramen restaurant on site "
United States
Kim
The price is Rp3.159.896
Rp3.475.885 total
includes taxes & fees
9 Feb - 10 Feb
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, (104 reviews)
  • cleanliness
    Ski in, ski out at this Vermont resort with direct access to mountain trails.
"Great resort "
United States
Adam
The price is Rp4.378.920
Rp4.773.023 total
includes taxes & fees
22 Feb - 23 Feb
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, (1,006 reviews)
  • cleanliness
    Convenient Rutland retreat with indoor pool near train station and dining.
"great hotel"
United States
Shweta
The price is Rp2.562.510
Rp2.818.761 total
includes taxes & fees
22 Feb - 23 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, (1,002 reviews)
  • cleanliness
    Enjoy a Vermont getaway with free breakfast near Green Mountain Shopping Plaza.
"Had a great stay"
United States
Jeff
The price is Rp2.133.039
Rp2.346.343 total
includes taxes & fees
10 Mar - 11 Mar
Days Inn by Wyndham Rutland/Killington Area
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (552 reviews)
  • cleanliness
    Find peace in Middlebury with convenient dining options and helpful staff.
"Laundry service was efficient and parking was easy "
United States
Agnes
The price is Rp2.105.250
Rp2.315.775 total
includes taxes & fees
15 Feb - 16 Feb
Courtyard Middlebury
Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (562 reviews)
  • cleanliness
    Elegant Woodstock retreat with golf, spa services, and idyllic central setting.
"Excellent hotel, staff well trained. "
United States
Christian
The price is Rp5.204.178
Rp6.465.644 total
includes taxes & fees
22 Feb - 23 Feb
Woodstock Inn & Resort
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)
  • cleanliness
    Serene ski hotel with complimentary shuttles and daily buffet breakfast.
"Very good place to stay "
United States
Barbara
The price is Rp2.485.879
Rp2.734.467 total
includes taxes & fees
10 Mar - 11 Mar
Best Western Inn & Suites Rutland-Killington
Iron/ironing board, free WiFi, bed sheets

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (912 reviews)
  • cleanliness
    Picturesque Woodstock retreat offers free bikes, hiking trails, and winter sports.
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,005 reviews)
  • cleanliness
    Riverside escape with indoor pool and bistro dining just steps from Woodstock.
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
The price is Rp3.999.612
Rp5.018.416 total
includes taxes & fees
16 Feb - 17 Feb
On The River Inn
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, (556 reviews)
  • cleanliness
    Great ski lodge with comfortable, quiet rooms just outside charming Woodstock.
"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 Rp1.230.260
Rp2.408.036 total
includes taxes & fees
9 Feb - 10 Feb
Sleep Woodstock Motel
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (997 reviews)
  • cleanliness
    Unwind in Rutland with complimentary breakfast and convenient indoor swimming.
"Room was very clean. Staff was very kind, professional. Will most likely stay here again."
United States
Bob
The price is Rp2.472.069
Rp2.719.277 total
includes taxes & fees
10 Mar - 11 Mar
Hampton Inn Rutland
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (264 reviews)
  • cleanliness
    Colonial elegance near Union Arena with beautiful garden and evening drinks.
"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, (61 reviews)
  • cleanliness
    Lincoln Inn offers charming riverside comfort in Woodstock, with free perks to enjoy.
"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 Rp2.425.248
Rp2.667.773 total
includes taxes & fees
8 Feb - 9 Feb
Lincoln Inn & Gallery
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (390 reviews)
  • cleanliness
    Experience sweet dreams at this charming motel in Middlebury near local theatre.
"Friendly staff, clean, comfortable and convenient to downtown. "
United States
Melissa
The price is Rp2.019.356
Rp2.221.291 total
includes taxes & fees
8 Feb - 9 Feb
Middlebury Sweets Motel
Front of property

Cortina Inn

Cortina Inn
3.0 star property
Rutland
6.6 out of 10, (684 reviews)
"Very quiet and comfortable stay."
United States
James
The price is Rp2.004.198
Rp2.204.618 total
includes taxes & fees
11 Feb - 12 Feb
Cortina Inn
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (418 reviews)
  • cleanliness
    Cosy Vermont retreat near Killington with seasonal pool and outdoor charm.
"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 Rp3.663.977
Rp3.993.734 total
includes taxes & fees
10 Mar - 11 Mar
The Vermont Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
  • cleanliness
    Charming B&B in Woodstock with complimentary breakfast and perfect location.
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is Rp5.035.758
Rp5.539.333 total
includes taxes & fees
9 Feb - 10 Feb
Stay At Jimmy's
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
  • cleanliness
    Enjoy a cosy Woodstock B&B with free breakfast, WiFi, and winter sports nearby.
"Charming bed and breakfast"
United States
Nicholas
The price is Rp3.126.212
Rp3.438.968 total
includes taxes & fees
10 Feb - 11 Feb
The Vesper
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (582 reviews)
  • cleanliness
    Enjoy a relaxing retreat in Brandon with a poolside terrace and complimentary dining.
"Beautiful and unique space, perfect for a weekend getaway in Vermont! "
United States
Sarah
The price is Rp2.014.303
Rp2.215.734 total
includes taxes & fees
11 Feb - 12 Feb
Brandon Inn
Exterior

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (332 reviews)
  • cleanliness
    A rustic New England inn near Vermont's natural attractions offers comfort and charm.
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
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
"Wonderful staff, fabulous food, lovely setting! We had a wonderful stay at the Inn over the holidays! Daughter and I had a Spa treatment as well. I also lost a hat on property, the housekeeping staff found it and the Inn mailed it back! 10/10 would recommend!"
Elizabeth 2-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 Rp1.626.678 per night from 2 Mar to 3 Mar
Rp1.626.678
Rp1.773.079 total
2 Mar - 3 Mar
includes taxes & fees
9.2/10 Wonderful! (375 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 Best Western Inn & Suites Rutland-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?
Best Western Inn & Suites Rutland-Killington: Provides buffet, a seasonal outdoor pool and free self parking. Woodstock Inn & Resort and Comfort Inn Rutland - 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 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. You'll also find Gifford Woods State Park and Fire Tower 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.