Search Pittsfield hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
This weekend
14 Nov - 16 Nov
Next weekend
21 Nov - 23 Nov

Filter by

Guest rating
Guest rating
Star rating

Top hotels and accommodation in Pittsfield

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is NZ$1,670
includes taxes & fees
15 Nov - 16 Nov
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, (1002)
"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 NZ$313
includes taxes & fees
23 Nov - 24 Nov
Best Western Inn & Suites Rutland-Killington
Room, 1 King Bed, Non Smoking
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 star property
Rutland
6.4 out of 10, (1000)
"I would rate this place as a B hotel. The hotel is over priced. "
Canada
Brett
The price is NZ$213
includes taxes & fees
23 Nov - 24 Nov
Days Inn by Wyndham Rutland/Killington Area
Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 star property
Rutland
8.0 out of 10, Very good, (1002)
"Clean, great steak house by the hotel"
United States
Caridad
The price is NZ$227
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Rutland - Killington
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (549)
"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 NZ$717
includes taxes & fees
15 Dec - 16 Dec
Woodstock Inn & Resort
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (541)
"Great motel with complete amenities.. beautiful surrounding especially in this fall"
United States
Giana
The price is NZ$239
includes taxes & fees
23 Nov - 24 Nov
Sleep Woodstock Motel
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (961)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is NZ$247
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn Rutland
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
Full-sized 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 NZ$190
includes taxes & fees
28 Nov - 29 Nov
My Place Hotel-Randolph VT
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 NZ$379
includes taxes & fees
16 Nov - 17 Nov
The Vermont 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 NZ$363
includes taxes & fees
23 Nov - 24 Nov
Mountain Meadows Lodge
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 NZ$214
includes taxes & fees
15 Dec - 16 Dec
Brandon Inn
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, (940)
"Excellent hotel. "
United States
Kristan
The price is NZ$266
includes taxes & fees
16 Nov - 17 Nov
The Mountain Inn at Killington
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, (1001)
"Room was spotless and comfortable. Dog friendly, hassle free stay. Cleanliness was top tier, and staff was fantastic!"
United States
Desiree
The price is NZ$285
includes taxes & fees
18 Nov - 19 Nov
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
The price is NZ$338
includes taxes & fees
11 Dec - 12 Dec
Summit Lodge
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1001)
"Loved all the Inn had to offer"
United States
Mark
The price is NZ$526
includes taxes & fees
5 Dec - 6 Dec
On The River Inn
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 NZ$192
includes taxes & fees
15 Nov - 16 Nov
Cortina Inn
Standard Room, 2 Double Beds
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
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 NZ$454
includes taxes & fees
23 Nov - 24 Nov
The Mountain Top Inn & Resort
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 NZ$387
includes taxes & fees
16 Nov - 17 Nov
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.
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

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.
See properties

Top Pittsfield Hotel Reviews

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"Loved the whole hotel staff was great and very helpful and it was very clean!!!"
Joseph 1-night trip
Posted 3 days ago
Hampton Inn Rutland

More cheap accommodation in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St, Rutland, VT
The price is NZ$227 per night from 10 Dec to 11 Dec
NZ$227
10 Dec - 11 Dec
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 traveller data. Two other choices for your trip to the area are Comfort Inn Rutland - Killington and Woodstock Inn & Resort. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning: This holiday home rental outside of Pittsfield 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 holiday with 1 hot tub and table football. See all 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?
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 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 40 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 Gifford Woods State Park and Pico Mountain at Killington Ski Resort 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.

Explore a world of travel with Expedia