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Compare 1,736 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is ￥62,774
￥145,694 total
includes taxes & fees
Nov 14 - Nov 15
The Getaway 4 Bedroom Home
Lobby
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 star property
Rutland
8.8 out of 10, Excellent, (1001)
"Fantastic place to stay. It was clean, comfortable and inviting. Staff were friendly and hospitable. Would stay here again! "
United States
Elexis
The price is ￥24,821
￥27,303 total
includes taxes & fees
Nov 19 - Nov 20
Best Western Inn & Suites Rutland-Killington
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very Good, (1007)
"Clean, great steak house by the hotel"
United States
Caridad
The price is ￥16,893
￥18,581 total
includes taxes & fees
Dec 4 - Dec 5
Comfort Inn Rutland - Killington
Room, 1 King Bed, Non Smoking | Desk, blackout drapes, iron/ironing board, free cribs/infant beds
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
Rutland
6.4 out of 10, (1006)
"I would rate this place as a B hotel. The hotel is over priced. "
Canada
Brett
The price is ￥16,893
￥18,582 total
includes taxes & fees
Nov 17 - Nov 18
Days Inn by Wyndham Rutland/Killington Area
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (548)
"I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn"
United States
Kevin
The price is ￥53,767
￥65,923 total
includes taxes & fees
Nov 19 - Nov 20
Woodstock Inn & Resort
Deluxe Suite | 2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (540)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is ￥15,945
￥24,320 total
includes taxes & fees
Nov 16 - Nov 17
Sleep Woodstock Motel
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (959)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is ￥19,966
￥21,962 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Rutland
Full-size fridge, microwave, stovetop, coffee/tea maker
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (329)
"Everything was outstanding!"
United States
Caroline E.
The price is ￥15,179
￥16,545 total
includes taxes & fees
Nov 28 - Nov 29
My Place Hotel-Randolph VT
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (881)
"Upon entering the hotel, the lobby is gorgeous with 2 fireplaces. Staff was super friendly and the free breakfast was a bonus. The room was spotless and has a fireplace in the room. My wife and I loved this place and will definitely go back. "
United States
Vincent
The Shire Woodstock
Front of property
The Vermont Inn

The Vermont Inn

3.0 star property
Rutland
9.2 out of 10, Wonderful, (412)
"The innkeepers were extremely personable, helpful and communicative. We will definitely stay again when we come to Vermont!"
United States
Anthony
The price is ￥31,197
￥34,006 total
includes taxes & fees
Nov 17 - Nov 18
The Vermont Inn
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (556)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is ￥16,953
￥18,648 total
includes taxes & fees
Nov 19 - Nov 20
Brandon Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (171)
"Lovely property and the staff members were extremely friendly"
United States
Christine
The price is ￥25,250
￥31,627 total
includes taxes & fees
Nov 17 - Nov 18
Mountain Meadows Lodge
Terrace/patio
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, (1000)
"Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!"
United States
Desiree
The price is ￥22,487
￥24,736 total
includes taxes & fees
Nov 30 - Dec 1
Killington Mountain Lodge, Tapestry Collection by Hilton
Fireplace
Summit Lodge

Summit Lodge

3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"Love the old ski lodge feel and the layout of the hotel"
United States
Joanne
Summit Lodge
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, (937)
"Excellent hotel. "
United States
Kristan
The price is ￥20,659
￥23,862 total
includes taxes & fees
Nov 18 - Nov 19
The Mountain Inn at Killington
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1004)
"Loved all the Inn had to offer"
United States
Mark
The price is ￥36,512
￥45,812 total
includes taxes & fees
Nov 14 - Nov 15
On The River Inn
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
North Star Lodge and Resort

North Star Lodge and Resort

2.0 star property
Killington
8.6 out of 10, Excellent, (1000)
"Was perfect for our one night stay "
United Kingdom
Ian
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, (93)
"We had a great time! Gorgeous view and everybody was super friendly and helpful!"
United States
Courtney
The price is ￥36,358
￥39,630 total
includes taxes & fees
Nov 17 - Nov 18
The Mountain Top Inn & Resort
Front of property
Cortina Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (639)
"The property is well located, but seems to have had better years in the past."
United States
Luis
The price is ￥15,252
￥16,777 total
includes taxes & fees
Nov 14 - Nov 15
Cortina Inn
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Superb stay in all ways!"
United States
Scott
The price is ￥30,658
￥33,724 total
includes taxes & fees
Nov 17 - Nov 18
Stay At Jimmy's
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

Pittsfield Town Hall

After visiting Pittsfield Town Hall, make a plan to see the other sights and activities in Pittsfield.
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Top Pittsfield Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Large, clean room with nice view. Unique. "
Vicki 1-night trip
Posted 3 days ago
The Shire Woodstock

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St, Rutland, VT
The price is ￥16,893 per night from Dec 4 to Dec 5
￥16,893
￥18,581 total
Dec 4 - Dec 5
includes taxes & fees
8/10 Very Good! (1,002 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 traveler data. Other good choices for your stay in the area are Comfort Inn Rutland - Killington and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.
What's the top vacation rental in Pittsfield?
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning: Located near Pittsfield, this vacation home rental is located near skiing and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven. You can relax into your vacation with a hot tub and foosball. See all 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: Provides continental, an indoor pool, and free self parking. Woodstock Inn & Resort and The Mountain Inn at Killington 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 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.

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