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

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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul

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Star rating

Our top choices for Pittsfield hotels

Hotel
Free daily buffet breakfast

Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,008 reviews)
"Nice comfortable bed, nice selection of breakfast items"
United States
Hawley
The price is ąøæ4,810
ąøæ5,291 total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn Rutland
Lobby

Middlebury Sweets Motel

Middlebury Sweets Motel
2.5 star property
Middlebury
8.6 out of 10, Excellent, (402 reviews)
"Clean room, friendly staff,helpful resources listed."
United States
Michael
The price is ąøæ4,578
ąøæ5,036 total
includes taxes & fees
15 Jul - 16 Jul
Middlebury Sweets Motel
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (580 reviews)
"Clean room, helpful staff, good restaurants, onsite guest laundry."
United States
Anne
The price is ąøæ5,064
ąøæ5,570 total
includes taxes & fees
2 Aug - 3 Aug
Courtyard Middlebury
Lobby

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very good, (1,007 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is ąøæ4,080
ąøæ4,488 total
includes taxes & fees
26 Jul - 27 Jul
Comfort Inn Rutland - Killington
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, (484 reviews)
"Great stay for passing through. Itā€™s super clean and great dog friendly option"
United States
John
The price is ąøæ4,614
ąøæ5,030 total
includes taxes & fees
2 Aug - 3 Aug
My Place Hotel-Randolph VT
Lobby

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
6.8 out of 10, (1,003 reviews)
"The staff was amazing!!! We will book this again in our next travels up!"
United States
Carol
The price is ąøæ4,165
ąøæ4,581 total
includes taxes & fees
13 Jul - 14 Jul
Days Inn by Wyndham Rutland/Killington Area
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, (1,012 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is ąøæ4,465
ąøæ5,157 total
includes taxes & fees
19 Jul - 20 Jul
The Mountain Inn at Killington
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 ąøæ5,034
ąøæ5,537 total
includes taxes & fees
15 Jul - 16 Jul
Best Western Inn & Suites Rutland-Killington
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 ąøæ5,826
ąøæ6,409 total
includes taxes & fees
14 Jul - 15 Jul
Inn at Neshobe River
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,007 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
The price is ąøæ8,623
ąøæ10,218 total
includes taxes & fees
11 Aug - 12 Aug
On The River Inn
Terrace/patio

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (7 reviews)
"Historical charm combined with Immaculate styleā€”- killer food hospitality highly recommend this placeā€”- so wonderful"
United States
Christine
The price is ąøæ5,625
ąøæ6,132 total
includes taxes & fees
19 Jul - 20 Jul
Green Trails Inn
Lobby sitting area

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,003 reviews)
"Great staff. Great breakfast."
United States
Kate
The price is ąøæ3,795
ąøæ4,175 total
includes taxes & fees
15 Jul - 16 Jul
Mountain Sports Inn
Fireplace

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,004 reviews)
"It was a very nice and comfortable stay Lee at the front desk was extremely"
United States
shaya
The price is ąøæ4,120
ąøæ4,532 total
includes taxes & fees
13 Jul - 14 Jul
North Star Lodge and Resort
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, (121 reviews)
"Excellent stay "
United States
Kristen
The price is ąøæ10,820
ąøæ11,794 total
includes taxes & fees
14 Jul - 15 Jul
The Mountain Top Inn & Resort
Elite Cabin, 1 King Bed, Sauna | Individually decorated, individually furnished, laptop workspace

Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
9.0 out of 10, Wonderful, (100 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 ąøæ5,393
ąøæ6,095 total
includes taxes & fees
26 Jul - 27 Jul
Emrose Luxury Cabins
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (654 reviews)
"Wonderful hosts, nice historic inn in quaint town"
United States
Katherine
The price is ąøæ5,021
ąøæ5,523 total
includes taxes & fees
14 Jul - 15 Jul
Brandon Inn
Interior detail

The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (155 reviews)
"Great room - very clean and comfortable. Helpful and welcoming staff - even left out breakfast for our early departure."
United States
Niall
The price is ąøæ5,304
ąøæ5,834 total
includes taxes & fees
14 Jul - 15 Jul
The Trailside Inn
Exterior

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (336 reviews)
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
The price is ąøæ8,779
ąøæ9,657 total
includes taxes & fees
13 Jul - 14 Jul
Kedron Valley Inn
Exterior

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, (1,001 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."
United States
Nicole
The price is ąøæ5,176
ąøæ5,694 total
includes taxes & fees
19 Jul - 20 Jul
Killington Mountain Lodge, Tapestry Collection by Hilton
Lake view

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (238 reviews)
"Great property for a nice getaway, plenty of amenities and the staff is top notch. Highly recommend"
United States
Scott
The price is ąøæ5,391
ąøæ6,762 total
includes taxes & fees
4 Aug - 5 Aug
Mountain Meadows Lodge
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

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Staff was very friendly and helpful"
Wendy 1-night trip
Posted 1 hour ago
Hampton Inn Rutland

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is ąøæ4,080 per night from 26 Jul to 27 Jul
ąøæ4,080
ąøæ4,488 total
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very good! (1,007 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.
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 17Ā°C, while the coldest months are January and February, with an average of -5Ā°C. The snowiest months in Pittsfield are January, March, February and December, with each month seeing an average of 26 cm of snowfall.