Pittsfield Hotels from S$122

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21 Aug - 22 Aug
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Top 10 trending Pittsfield hotels

Days Inn by Wyndham Rutland/Killington Area
1 bedroom, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1006)
"Clean and comfortable. Good value for what you get. Would stay again. "
The price is S$143
includes taxes & fees
25 Aug - 26 Aug
Days Inn by Wyndham Rutland/Killington Area
My Place Hotel-Randolph VT
Full-sized fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (254)
"Very clean and the beds were comfortable. "
The price is S$227
includes taxes & fees
3 Sept - 4 Sept
My Place Hotel-Randolph VT
Best Western Inn & Suites Rutland-Killington
Lobby

Best Western Inn & Suites Rutland-Killington

2.5 star property
8.8 out of 10, Excellent, (1000)
"I liked it was like staying in a condo. "
The price is S$223
includes taxes & fees
3 Sept - 4 Sept
Best Western Inn & Suites Rutland-Killington
Comfort Inn Rutland - Killington
Exterior

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1003)
"Staff was very friendly and very helpful we had a pleasant stay."
The price is S$177
includes taxes & fees
24 Aug - 25 Aug
Comfort Inn Rutland - Killington
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (531)
"Relaxing "
The price is S$635
includes taxes & fees
1 Sept - 2 Sept
Woodstock Inn & Resort
Sleep Woodstock Motel
2 bedrooms, individually decorated, desk, blackout curtains

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (512)
"Charming, clean, great location and price"
The price is S$168
includes taxes & fees
25 Aug - 26 Aug
Sleep Woodstock Motel
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (809)
"Enjoyed our stay and will return"
The Shire Woodstock
Cortina Inn
Front of property

Cortina Inn

3.0 star property
6.8 out of 10, (595)
"Staff were extremely helpful all during my stay."
The price is S$122
includes taxes & fees
28 Aug - 29 Aug
Cortina Inn
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (506)
"Great stay"
The price is S$200
includes taxes & fees
25 Aug - 26 Aug
Brandon Inn
Hampton Inn Rutland
Exterior

Hampton Inn Rutland

2.5 star property
9.0 out of 10, Wonderful, (933)
"The staff were helpful and morning breakfast very good. "
The price is S$212
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn Rutland
The Mountain Inn at Killington
Breakfast and dinner served

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (872)
"Clean and very friendly, capable staff. 👍"
The Mountain Inn at Killington
Lincoln Inn & Gallery
Interior

Lincoln Inn & Gallery

3.0 star property
9.4 out of 10, Exceptional, (31)
"This place was great I cannot say enough about the innkeepers and the staff all in all you'll love it!!"
The price is S$235
includes taxes & fees
24 Aug - 25 Aug
Lincoln Inn & Gallery
Mountain Meadows Lodge
Lake view

Mountain Meadows Lodge

3.5 star property
9.4 out of 10, Exceptional, (144)
"This is a beautiful newly renovated inn in a gorgeous location"
The price is S$253
includes taxes & fees
24 Aug - 25 Aug
Mountain Meadows Lodge
North Star Lodge and Resort
Iron/ironing board, free WiFi, bed sheets

North Star Lodge and Resort

2.0 star property
8.6 out of 10, Excellent, (1000)
"Great place to stay"
North Star Lodge and Resort
Courtyard Middlebury
Exterior

Courtyard Middlebury

3.0 star property
8.8 out of 10, Excellent, (522)
"Daily or at least every other day housekeeping service would have been appreciated. "
The price is S$202
includes taxes & fees
7 Sept - 8 Sept
Courtyard Middlebury
Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (923)
"Clean, quiet stay."
The price is S$133
includes taxes & fees
25 Aug - 26 Aug
Mountain Sports Inn
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.4 out of 10, Good, (1000)
"Views were spectacular "
The price is S$196
includes taxes & fees
1 Sept - 2 Sept
Killington Mountain Lodge, Tapestry Collection by Hilton
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (39)
"Superb stay in all ways!"
The price is S$281
includes taxes & fees
28 Aug - 29 Aug
Stay At Jimmy's
The Mountain Top Inn & Resort
Living area

The Mountain Top Inn & Resort

3.5 star property
9.2 out of 10, Wonderful, (87)
"Great views and food. "
The price is S$455
includes taxes & fees
27 Aug - 28 Aug
The Mountain Top Inn & Resort
On The River Inn
Private kitchen

On The River Inn

4.0 star property
9.4 out of 10, Exceptional, (1002)
"Great location, very quiet with good breakfast choices. "
On The River 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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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

Top Pittsfield Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The hotel is very nice, very friendly, beautiful views specially from the room with balcony. Game room is awesome and the breakfast was delicious. Will come back again. "
DANIEL 2-night trip
Posted 14 hours ago
The Mountain Inn at Killington

Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are The Shire Woodstock and Days Inn by Wyndham Rutland/Killington Area. 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: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Days Inn by Wyndham Rutland/Killington Area and North Star Lodge and 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, 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.