Pittsfield Hotels

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Check prices for these dates

Tonight
Mar 23 - Mar 24
Tomorrow
Mar 24 - Mar 25
Next weekend
Mar 28 - Mar 30
In two weeks
Apr 4 - Apr 6

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Top 10 trending Pittsfield hotels

The Getaway 4 Bedroom Home
Exterior

The Getaway 4 Bedroom Home

3.0 star property
The price is P15,052
P44,430 total
includes taxes & fees
Mar 24 - Mar 25
The Getaway 4 Bedroom Home
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (28)
"We spent a wonderful week at Stay at Jimmy’s, with our dog Sofia (they are super dog friendly) and it was the perfect escape. From the moment we arrived, the hospitality was top-notch. The Relax Room was absolutely amazing—the whirlpool tub was the best we’ve ever used, making it the ideal place to unwind. Every morning, we were treated to fresh-baked goods, a great selection of teas, coffee, and soft drinks, which made us feel right at home. The attention to detail in the interior design was...
The price is P11,411
P12,552 total
includes taxes & fees
Mar 24 - Mar 25
Stay At Jimmy's
The Shire Woodstock
Property grounds

The Shire Woodstock

3.0 star property
8.8 out of 10, Excellent, (733)
"Great stay!"
The price is P8,388
P9,780 total
includes taxes & fees
Apr 1 - Apr 2
The Shire Woodstock
The Vesper
Individually decorated, individually furnished, free WiFi, bed sheets

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (15)
"Charming inn, great service"
The price is P8,063
P8,870 total
includes taxes & fees
Mar 25 - Mar 26
The Vesper
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (504)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is P17,145
P21,382 total
includes taxes & fees
Apr 6 - Apr 7
Woodstock Inn & Resort
The Jackson
Fireplace

The Jackson

4.0 star property
9.8 out of 10, Exceptional, (207)
"Beautiful property with wonderful attention to detail and warm, friendly staff — really enjoyed our stay! Woodstock is a charming town and The Jackson staff offered great local recommendations in addition to providing comfortable lodging with thoughtful amenities, delicious breakfast and pretty views. Thank you to Dave and team — highly recommend!"
The price is P11,376
P12,514 total
includes taxes & fees
Mar 24 - Mar 25
The Jackson
506 On the River Inn
Private kitchen

506 On the River Inn

4.0 star property
9.4 out of 10, Exceptional, (981)
"Great breakfast and extremely quiet "
The price is P12,850
P14,135 total
includes taxes & fees
Mar 24 - Mar 25
506 On the River Inn
Lincoln Inn & Gallery
Free WiFi

Lincoln Inn & Gallery

The price is P10,895
P11,984 total
includes taxes & fees
Mar 24 - Mar 25
Lincoln Inn & Gallery
Sleep Woodstock Motel
Individually decorated, desk, blackout drapes, iron/ironing board

Sleep Woodstock Motel

2.0 star property
9.6 out of 10, Exceptional, (475)
"Great motel that is much nicer than your typical motel"
The price is P5,849
P7,380 total
includes taxes & fees
Mar 24 - Mar 25
Sleep Woodstock Motel
Echo Lake Inn
Exterior

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (96)
"Old fashioned inn with wonderful hosts."
The price is P16,712
P18,216 total
includes taxes & fees
Mar 24 - Mar 25
Echo Lake Inn
Intrepid Angel Farm Cottage In Bridgewater Corners 2 Bedroom Home
Exterior

Intrepid Angel Farm Cottage In Bridgewater Corners 2 Bedroom Home

3.0 star property
The price is P17,009
P49,133 total
includes taxes & fees
Mar 24 - Mar 25
Intrepid Angel Farm Cottage In Bridgewater Corners 2 Bedroom Home
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, (171)
"It was new, clean, and check in was easy. The room was comfortable and clean. I would stay here again if I was traveling this way again and needed a place to stay."
The price is P6,657
P7,256 total
includes taxes & fees
Apr 13 - Apr 14
My Place Hotel-Randolph VT
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Living area

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

3.0 star property
The price is P20,847
P61,411 total
includes taxes & fees
Mar 24 - Mar 25
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo
Private kitchen

Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is P14,977
P41,617 total
includes taxes & fees
Mar 31 - Apr 1
Sunrise Timberline: 3br, 2ba Ski In/ski Out Condo 3 Bedroom Condo
Turn of River Lodge
Interior

Turn of River Lodge

2.5 star property
9.0 out of 10, Wonderful, (250)
"Perfect for what i wanted - a bed to sleep"
The price is P6,623
P7,286 total
includes taxes & fees
Apr 1 - Apr 2
Turn of River Lodge
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Private kitchen

Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

3.0 star property
The price is P13,772
P40,041 total
includes taxes & fees
Mar 31 - Apr 1
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Fall Line Condo D1 1 Bedroom Condo
Exterior

Fall Line Condo D1 1 Bedroom Condo

3.5 star property
The price is P8,730
P25,115 total
includes taxes & fees
Mar 24 - Mar 25
Fall Line Condo D1 1 Bedroom Condo
Fall Line Condo E1 1 Bedroom Condo
Exterior

Fall Line Condo E1 1 Bedroom Condo

3.5 star property
The price is P9,407
P27,858 total
includes taxes & fees
Mar 24 - Mar 25
Fall Line Condo E1 1 Bedroom Condo
Fall Line Condo B2 3 Bedroom Condo
Exterior

Fall Line Condo B2 3 Bedroom Condo

3.5 star property
4.0 out of 10, (1)
"This property should not be rented and I body ever got back to us and toilet was broken. You shouldn’t market this on Expedia. "
The price is P18,815
P43,614 total
includes taxes & fees
Mar 31 - Apr 1
Fall Line Condo B2 3 Bedroom Condo
Fall Line Condos by Killington VR - 2 Bedrooms
Exterior

Fall Line Condos by Killington VR - 2 Bedrooms

3.5 star property
The price is P8,655
P30,315 total
includes taxes & fees
Mar 24 - Mar 25
Fall Line Condos by Killington VR - 2 Bedrooms
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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Frequently asked questions

Where is the best place to stay in Pittsfield?

Located 14.4 mi (23.2 km) from the heart of Pittsfield, Comfort Inn Rutland - Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Killington Mountain Lodge, Tapestry Collection by Hilton and My Place Hotel-Randolph VT. 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?

Comfort Inn Rutland - Killington: Features buffet, an indoor pool, and free self parking. Days Inn by Wyndham Rutland/Killington Area and Woodstock Inn & 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 40 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 Appalachian Trail Adventures and Green Mountain National Golf Course 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.