Find hotels in Pittsfield, VT from ₩158,919

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Feb 28 - Mar 1
Tomorrow
Mar 1 - Mar 2
Next weekend
Mar 6 - Mar 8
In two weeks
Mar 13 - Mar 15

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Pittsfield hotels

Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (557 reviews)
"So much love and thoughtfulness was put into our room and common area. Comfy beds, little touches like free snacks and goodies and super clean room. It's also super dog friendly! There's also a fantastic little coffee stand walking distance. "
United States
JILL
The price is ₩115,342
₩216,874 total
includes taxes & fees
Mar 2 - Mar 3
Sleep Woodstock Motel
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ₩265,836
₩292,431 total
includes taxes & fees
Mar 11 - Mar 12
The Vesper
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,000 reviews)
"Everything was amazing from the room to the pool to the restaurant and staff. "
United States
Ilana
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (271 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
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, (397 reviews)
"Room was spacious and clean, convenient to highway and restaurants"
United States
ALAN
The price is ₩145,797
₩158,919 total
includes taxes & fees
Mar 23 - Mar 24
My Place Hotel-Randolph VT
Iron/ironing board, free WiFi, bed sheets

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (914 reviews)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
Exterior

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (333 reviews)
"Clean very well decorated room with comfortable beds and lots of pillows. Would stay again "
United States
Andrew
Kedron Valley Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is ₩336,555
₩370,211 total
includes taxes & fees
Mar 10 - Mar 11
Deer Brook Inn
Lobby sitting area

Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
West Woodstock
8.6 out of 10, Excellent, (63 reviews)
"The accommodations are perfect for a weekend away and less than a 20 minute drive to Killington resort!! It is a very warm and cute stay"
United States
Ronda
The price is ₩207,355
₩228,090 total
includes taxes & fees
Mar 1 - Mar 2
Lincoln Inn & Gallery
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ₩428,213
₩471,034 total
includes taxes & fees
Mar 31 - Apr 1
Stay At Jimmy's
Property grounds

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (199 reviews)
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
The price is ₩157,537
₩178,017 total
includes taxes & fees
Mar 31 - Apr 1
Mountain Valley Retreat
Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (565 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is ₩444,951
₩552,805 total
includes taxes & fees
Mar 22 - Mar 23
Woodstock Inn & Resort
Property entrance

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The price is ₩383,478
₩421,824 total
includes taxes & fees
Mar 21 - Mar 22
The Woodstocker B&B
Lobby sitting area

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,003 reviews)
"All wonderful for a two day stay!"
United States
Charles
The price is ₩156,104
₩171,714 total
includes taxes & fees
Mar 30 - Mar 31
Mountain Sports Inn
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ₩209,523
₩545,548 total
includes taxes & fees
Mar 2 - Mar 3
The Suites at Killington Center
Interior

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (283 reviews)
"Great place "
United States
Matthew
The price is ₩181,167
₩199,298 total
includes taxes & fees
Mar 4 - Mar 5
Turn of River Lodge
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (99 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is ₩419,694
₩457,467 total
includes taxes & fees
Mar 2 - Mar 3
Echo Lake Inn
Exterior detail

Killington Haus

Killington Haus
2.0 star property
Killington
8.4 out of 10, Very Good, (18 reviews)
"Great location to ski resort and excellent Ramen restaurant on site "
United States
Kim
The price is ₩253,176
₩278,493 total
includes taxes & fees
Mar 2 - Mar 3
Killington Haus
Reception

Grey Bonnet Inn

Grey Bonnet Inn
2.0 star property
Killington
8.0 out of 10, Very Good, (75 reviews)
"Good communication "
United States
Michelle
The price is ₩234,901
₩258,388 total
includes taxes & fees
Mar 9 - Mar 10
Grey Bonnet Inn
Garden

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,004 reviews)
"Staff was helpful and room was clean"
United States
Gerry
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Stay near popular Pittsfield attractions

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
See properties

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

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"all of it"
ariana 1-night trip
Posted 2 days ago
My Place Hotel-Randolph VT

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is ₩145,797 per night from Mar 23 to Mar 24
₩145,797
₩158,919 total
Mar 23 - Mar 24
includes taxes & fees
9.4/10 Exceptional! (397 reviews)

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 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: Offers continental, an indoor pool, and free self parking. Best Western Inn & Suites Rutland-Killington 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 41 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, Pittsfield Town Hall, and Roger Clark Memorial Central Library. You'll also find Gifford Woods State Park and Pico Mountain at Killington Ski Resort 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.