Pittsfield Hotels from S$145

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Check prices for these dates

Tonight
12 Jan - 13 Jan
Tomorrow
13 Jan - 14 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

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Our top choices for Pittsfield hotels

Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The price is S$1,304
includes taxes & fees
13 Jan - 14 Jan
The Getaway 4 Bedroom Home
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (193 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 S$160
includes taxes & fees
13 Jan - 14 Jan
Mountain Valley Retreat
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (903 reviews)
"Wonderful place to stay!"
United States
Robin
The price is S$194
includes taxes & fees
25 Jan - 26 Jan
The Shire Woodstock
Private kitchen
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (553 reviews)
"The staff at this motel are 5 star! Lisa went above and beyond to make my stay easy since I was there for a medical procedure. "
United States
Crystal
The price is S$184
includes taxes & fees
15 Jan - 16 Jan
Sleep Woodstock Motel
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (261 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
Hallway
On The River Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,010 reviews)
"Brilliant stay"
United States
Enrico
The price is S$383
includes taxes & fees
12 Feb - 13 Feb
On The River Inn
Exterior
Kedron Valley Inn

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (330 reviews)
"Fantastic stay and staff!"
United States
Carrie
Kedron Valley Inn
Lobby sitting area
Lincoln Inn & Gallery

Lincoln Inn & Gallery

Lincoln Inn & Gallery
2.0 star property
West Woodstock
8.6 out of 10, Excellent, (58 reviews)
"A very pleasant VT stay at a reasonable price."
United States
Sean
The price is S$178
includes taxes & fees
13 Jan - 14 Jan
Lincoln Inn & Gallery
Interior
Turn of River Lodge

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
9.0 out of 10, Wonderful, (271 reviews)
"Was amazing ill be back"
United States
Jacob
The price is S$179
includes taxes & fees
13 Jan - 14 Jan
Turn of River Lodge
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (559 reviews)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is S$508
includes taxes & fees
19 Jan - 20 Jan
Woodstock Inn & Resort
Balcony
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (998 reviews)
"Staff was great and breakfast was excellent "
United States
Bruce
The price is S$154
includes taxes & fees
14 Jan - 15 Jan
Mountain Sports Inn
Exterior
Killington Mountain Lodge, Tapestry Collection by Hilton

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, (1,003 reviews)
"Good place to stay when you ski"
United States
Josh
The price is S$243
includes taxes & fees
19 Jan - 20 Jan
Killington Mountain Lodge, Tapestry Collection by Hilton
Garden
North Star Lodge and Resort

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,003 reviews)
"Good value, located near the slopes. "
United States
Angela
The price is S$204
includes taxes & fees
14 Jan - 15 Jan
North Star Lodge and Resort
Interior
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is S$226
includes taxes & fees
13 Jan - 14 Jan
The Vesper
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (375 reviews)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is S$333
includes taxes & fees
20 Jan - 21 Jan
Snowed Inn
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (406 reviews)
"Good location and close to ski area. Good free breakfast makes stay nicer. Staff are nice. "
United States
RAYMOND
The price is S$246
includes taxes & fees
13 Jan - 14 Jan
Summit Lodge
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (978 reviews)
"Great place to stay!"
United States
Stephen
The price is S$300
includes taxes & fees
15 Jan - 16 Jan
The Mountain Inn at Killington
Lounge
Greenbrier Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (652 reviews)
"Great location near the mountain, very cozy."
United States
Raphael
Greenbrier Inn
BBQ/picnic Area
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (364 reviews)
"Friendly staff, clean, very comfortable room."
United States
Jennifer
The price is S$145
includes taxes & fees
8 Feb - 9 Feb
My Place Hotel-Randolph VT
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46 reviews)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is S$353
includes taxes & fees
13 Jan - 14 Jan
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

Après Inn Killington

Après Inn Killington

10/10 Excellent
"Our room(s) were clean, with spotless white bedding. The weather was SUPER cold while we were there and yet the rooms stayed comfortably warm! Brett & Casey were very responsive to any questions we had and my 3-year old granddaughter insisted on meeting them! I received great advice on the local restaurants (with tips for beating the crowds) and also about the bus schedules. The hotel is located right next door to one of the most popular restaurants in the area! Thanks, guys! "
Eliza 2-night trip
Posted 5 days ago
Après Inn Killington

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is S$145 per night from 8 Feb to 9 Feb
S$145
8 Feb - 9 Feb
includes taxes & fees
9.2/10 Wonderful! (363 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 traveller data. Two other choices for your trip to the area are Killington Mountain Lodge, Tapestry Collection by Hilton and The Mountain Inn at Killington. 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, 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: Features continental, an indoor pool and free self parking. The Mountain Inn at Killington and Woodstock Inn & Resort 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. A top sight in the area is Killington Resort. In Pittsfield, there are 41 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. Additionally, you'll find Killington 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.

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