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Our top choices for Pittsfield hotels

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (1 review)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is NZ$213
includes taxes & fees
31 May - 1 June
Green Trails Inn

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (70 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is NZ$276
includes taxes & fees
19 May - 20 May
Lincoln Inn & Gallery

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (633 reviews)
"Quintessential Vermont Inn in a wonderful little town. We had a great stay! "
United States
Heidi
The price is NZ$207
includes taxes & fees
19 May - 20 May
Brandon Inn

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (448 reviews)
"Great location for us when visiting VT."
United States
Jeannine
The price is NZ$202
includes taxes & fees
3 June - 4 June
My Place Hotel-Randolph VT

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (579 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is NZ$206
includes taxes & fees
18 May - 19 May
Sleep Woodstock Motel

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (398 reviews)
"Hotel was very clean and unique. Room felt like it was recently redone, comfortable and nice. Candy store was amazing-very fun to look around"
United States
Victoria
The price is NZ$226
includes taxes & fees
20 May - 21 May
Middlebury Sweets Motel

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,009 reviews)
"Always love our stay - dog friendly and people friendly!"
United States
Hanna
The price is NZ$265
includes taxes & fees
21 May - 22 May
The Mountain Inn at Killington

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (61 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is NZ$401
includes taxes & fees
20 May - 21 May
The Vesper

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (280 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is NZ$253
includes taxes & fees
19 May - 20 May
The Jackson

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.4 out of 10, Exceptional, (16 reviews)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
United States
Keith
The price is NZ$330
includes taxes & fees
19 May - 20 May
Inn at Neshobe River

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,001 reviews)
"The room was clean and the staff was very helpful and friendly."
United States
Kevin
The price is NZ$261
includes taxes & fees
14 June - 15 June
Hampton Inn Rutland

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
"Great place"
United States
Peter
The price is NZ$205
includes taxes & fees
24 May - 25 May
Mountain Sports Inn

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,002 reviews)
"Breakfast was great and parking free and adequate!"
United States
Susan
The price is NZ$252
includes taxes & fees
25 May - 26 May
Comfort Inn Rutland - Killington

Killington Haus

Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (43 reviews)
"Very close to ski resort, 3-minute drive, and close to restaurants on Killington Road."
United States
Alex
The price is NZ$231
includes taxes & fees
31 May - 1 June
Killington Haus

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (93 reviews)
"Will definitely be back!! "
United States
Steevyann
The price is NZ$313
includes taxes & fees
20 May - 21 May
Emrose Luxury Cabins

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Plenty of space, storage, and nice kitchen. Room and bathroom was clean, bed was comfortable, and the heated pool with a view of the mountain was a huge plus after a long day of skiing"
United States
William
The price is NZ$250
includes taxes & fees
19 May - 20 May
North Star Lodge and Resort

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,007 reviews)
"Clean room, friendly staff, family-friendly. "
United States
Suwei
The price is NZ$397
includes taxes & fees
11 June - 12 June
On The River Inn

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (928 reviews)
"Lovely hotel with views of river and walkable to variety of shops and restaurants"
United States
Arlene
The price is NZ$280
includes taxes & fees
25 May - 26 May
The Shire Woodstock

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (568 reviews)
"Clean room, helpful staff, good restaurants, onsite guest laundry."
United States
Anne
The price is NZ$303
includes taxes & fees
14 June - 15 June
Courtyard Middlebury

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (188 reviews)
"Location is great"
United States
Lei
The price is NZ$260
includes taxes & fees
20 May - 21 May
Après Inn 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

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

autumn trees reflected in water

Top Pittsfield Hotel Reviews

More cheap accommodation in Pittsfield

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 Comfort Inn Rutland - Killington and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Killington area home - 4-seasons, hot tub and A/C: This highly rated holiday home rental in Pittsfield is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. 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. Woodstock Inn & Resort 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 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 Green Mountain National Golf Course and Gifford Woods State Park 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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