Pittsfield Hotels

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Aug 18 - Aug 19
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Top 10 trending Pittsfield hotels

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

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
6.4 out of 10, (1004)
"The gentleman that checked us in was great "
The price is P5,773
P6,351 total
includes taxes & fees
Aug 20 - Aug 21
Days Inn by Wyndham Rutland/Killington Area
My Place Hotel-Randolph VT
Full-size fridge, microwave, stovetop, coffee/tea maker

My Place Hotel-Randolph VT

2.0 star property
9.4 out of 10, Exceptional, (249)
"Very clean and the beds were comfortable. "
The price is P9,239
P10,071 total
includes taxes & fees
Aug 31 - Sep 1
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, (1002)
"I liked it was like staying in a condo. "
The price is P8,990
P9,889 total
includes taxes & fees
Sep 1 - Sep 2
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, (1008)
"Staff was very friendly and very helpful we had a pleasant stay."
The price is P7,140
P7,854 total
includes taxes & fees
Aug 24 - Aug 25
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 P23,344
P28,190 total
includes taxes & fees
Sep 1 - Sep 2
Woodstock Inn & Resort
Sleep Woodstock Motel
2 bedrooms, individually decorated, desk, blackout drapes

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (511)
"Charming, clean, great location and price"
The price is P5,907
P7,441 total
includes taxes & fees
Aug 21 - Aug 22
Sleep Woodstock Motel
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (805)
"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, (592)
"Staff were extremely helpful all during my stay."
The price is P6,113
P6,724 total
includes taxes & fees
Aug 19 - Aug 20
Cortina Inn
Brandon Inn
Exterior

Brandon Inn

3.0 star property
8.6 out of 10, Excellent, (505)
"Excellent stay!!"
The price is P8,607
P9,468 total
includes taxes & fees
Aug 19 - Aug 20
Brandon Inn
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 P9,503
P10,454 total
includes taxes & fees
Aug 24 - Aug 25
Lincoln Inn & Gallery
The Mountain Inn at Killington
Breakfast and dinner served

The Mountain Inn at Killington

2.5 star property
9.2 out of 10, Wonderful, (869)
"The staff was exceptional and will for sure come back again,"
The Mountain Inn at Killington
Hampton Inn Rutland
Exterior

Hampton Inn Rutland

2.5 star property
9.0 out of 10, Wonderful, (932)
"The staff were helpful and morning breakfast very good. "
The price is P8,490
P9,339 total
includes taxes & fees
Sep 7 - Sep 8
Hampton Inn Rutland
Mountain Meadows Lodge
Lake view

Mountain Meadows Lodge

3.5 star property
9.4 out of 10, Exceptional, (143)
"This is a beautiful newly renovated inn in a gorgeous location"
The price is P8,930
P11,249 total
includes taxes & fees
Aug 19 - Aug 20
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, (1006)
"Great place to stay"
North Star Lodge and Resort
Mountain Sports Inn
Front of property

Mountain Sports Inn

2.0 star property
8.8 out of 10, Excellent, (921)
"Super nice staff, and a good price. "
The price is P5,365
P5,902 total
includes taxes & fees
Aug 19 - Aug 20
Mountain Sports Inn
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 P8,168
P8,984 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard Middlebury
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, (1001)
"Views were spectacular "
The price is P7,910
P8,701 total
includes taxes & fees
Sep 1 - Sep 2
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 P11,358
P12,494 total
includes taxes & fees
Aug 25 - Aug 26
Stay At Jimmy's
The Mountain Top Inn & Resort
Living area

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (86)
"Great views and food. "
The price is P18,550
P20,220 total
includes taxes & fees
Aug 19 - Aug 20
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, (1001)
"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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Staff was very friendly and very helpful we had a pleasant stay."
David 1-night trip
Posted 2 days ago
Comfort Inn Rutland - 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 traveler data. Other good choices for your stay in 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, the majority of hotel reservations are fully refundable if cancelled before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Pittsfield.

Where can I learn more about changing or cancelling my trip to Pittsfield?

To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.

What's the best budget-friendly hotel in Pittsfield?

Based on reviews, Clear River Inn is a popular inn for our travelers who want a more economical choice, and features free WiFi and free parking. View all budget hotels in Pittsfield.

What's the best pet-friendly place to stay 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 accommodations 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 with an onsite pool. View all hotels with pools in Pittsfield.

What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?

Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.

What's it like 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 43 hotels and other accommodations to choose from. Find out more about Pittsfield.

What should I see while I'm in Pittsfield?

Favorite 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. Check out what more to see and do in Expedia's Pittsfield guide.

What's the seasonal weather like in Pittsfield?

The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.