A lake surrounded by autumn-colored trees and a rocky shoreline.

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Check prices for these dates

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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Our top choices for Pittsfield hotels

Terrace/patio

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (6 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is NZ$299
includes taxes & fees
28 July - 29 July
Green Trails 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, (1,004 reviews)
"Clean, comfortable and great location. Plus they have a hotel dog on staff!"
United States
Laura
The price is NZ$273
includes taxes & fees
9 July - 10 July
The Mountain Inn at Killington
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice comfortable bed, nice selection of breakfast items"
United States
Hawley
The price is NZ$253
includes taxes & fees
9 July - 10 July
Hampton Inn Rutland
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (647 reviews)
"Spacious comfortable family suite. Convenient location, clean beautiful inn, great customer service."
United States
Eva
The price is NZ$276
includes taxes & fees
5 July - 6 July
Brandon Inn
Deluxe Suite | Private kitchen

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (589 reviews)
"Quiet, well kept, comfortable, convenient."
United States
Elisabeth
The price is NZ$162
includes taxes & fees
5 July - 6 July
Sleep Woodstock Motel
Lobby sitting area

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Great place"
United States
Peter
The price is NZ$211
includes taxes & fees
9 July - 10 July
Mountain Sports Inn
Exterior

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.6 out of 10, Exceptional, (18 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$339
includes taxes & fees
4 July - 5 July
Inn at Neshobe River
Lobby

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.6 out of 10, (1,004 reviews)
"The staff was amazing!!! We will book this again in our next travels up!"
United States
Carol
The price is NZ$234
includes taxes & fees
5 July - 6 July
Days Inn by Wyndham Rutland/Killington Area
Exterior

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (99 reviews)
"Very nice, clean place to stay in Brandon. Visited family over the years and this was by far the best stay...."
United States
Tim
The price is NZ$323
includes taxes & fees
16 July - 17 July
Emrose Luxury Cabins
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (400 reviews)
"Clean room, friendly staff,helpful resources listed."
United States
Michael
The price is NZ$266
includes taxes & fees
7 July - 8 July
Middlebury Sweets Motel
BBQ/picnic Area

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (479 reviews)
"Great stay for passing through. It’s super clean and great dog friendly option"
United States
John
The price is NZ$247
includes taxes & fees
22 July - 23 July
My Place Hotel-Randolph VT
Lobby

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,001 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is NZ$244
includes taxes & fees
2 Aug - 3 Aug
Comfort Inn Rutland - Killington
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (291 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is NZ$312
includes taxes & fees
21 July - 22 July
The Jackson
Front of property

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (430 reviews)
"Clean, cozy, nice staff!"
United States
Mary
The price is NZ$374
includes taxes & fees
5 July - 6 July
The Vermont Inn
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (575 reviews)
"Clean room, helpful staff, good restaurants, onsite guest laundry."
United States
Anne
The price is NZ$277
includes taxes & fees
6 July - 7 July
Courtyard Middlebury
Lobby

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"Staff very friendly and helpful! Room was very clean and the bed is very comfortable!"
United States
katrina
The price is NZ$293
includes taxes & fees
8 July - 9 July
Best Western Inn & Suites Rutland-Killington
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (67 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
The price is NZ$339
includes taxes & fees
23 July - 24 July
The Vesper
Elite Room

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (76 reviews)
"Peaceful, historic property with amiable keepers."
United States
Elisabeth
The price is NZ$327
includes taxes & fees
6 July - 7 July
Lincoln Inn & Gallery
Lake view

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (236 reviews)
"Beautiful couple for hosts and stunning location. Great breakfast and hot tub to relax after a long drive. Will come back to stay longer"
Canada
Tanuja
The price is NZ$320
includes taxes & fees
8 July - 9 July
Mountain Meadows Lodge
Fireplace

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Great pool, bar, & staff!"
United States
Patrick
The price is NZ$266
includes taxes & fees
29 July - 30 July
North Star Lodge and Resort
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

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.

See all hotels in Pittsfield
A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

Recent Reviews in Pittsfield

Killington area home - 4-seasons, hot tub and A/C

Killington area home - 4-seasons, hot tub and A/C

10/10 Excellent
"Clean house"
Mark E. 5-night trip
Posted 3 hours ago
Killington area home - 4-seasons, hot tub and A/C

More cheap accommodation in Pittsfield

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

401 US-7 Rutland VT
The price is NZ$234 per night from 5 July to 6 July
NZ$234
5 July - 6 July
includes taxes & fees
6.6/10 (1,004 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 Woodstock Inn & Resort and The Mountain Inn at Killington. 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?
Woodstock Inn & Resort: Provides a seasonal outdoor pool, an indoor pool and 4 restaurants. The Mountain Inn at Killington and On The River Inn 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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