Pittsfield Hotels

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Nov 18 - Nov 19
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Nov 19 - Nov 20
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Top 10 trending Pittsfield hotels

Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

3.0 star property
Pittsfield
The price is P25,574
P57,759 total
includes taxes & fees
Nov 19 - Nov 20
The Getaway 4 Bedroom Home
Exterior
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 star property
Rutland
8.8 out of 10, Excellent, (1003)
"Was very nice the staff especially Jesica in front desk Talk me about alls the restaurants around the area "
United States
SANTIAGO
The price is P9,494
P10,443 total
includes taxes & fees
Dec 1 - Dec 2
Best Western Inn & Suites Rutland-Killington
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, (1001)
"I would rate this place as a B hotel. The hotel is over priced. "
Canada
Brett
The price is P6,962
P7,658 total
includes taxes & fees
Nov 24 - Nov 25
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, (1004)
"Clean, great steak house by the hotel"
United States
Caridad
The price is P6,862
P7,548 total
includes taxes & fees
Dec 10 - Dec 11
Comfort Inn Rutland - Killington
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (550)
"Highly recommend stay here"
United States
Margie
The price is P19,387
P23,918 total
includes taxes & fees
Dec 2 - Dec 3
Woodstock Inn & Resort
2 bedrooms, individually decorated, desk, blackout drapes
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (542)
"Clean, friendly, easy check in, welcoming accommodations. Can’t wait to come back"
United States
David
The price is P4,879
P7,960 total
includes taxes & fees
Nov 23 - Nov 24
Sleep Woodstock Motel
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (962)
"Very clean, good location, and super helpful staff!"
United States
Sheryl
The price is P7,512
P8,263 total
includes taxes & fees
Nov 25 - Nov 26
Hampton Inn Rutland
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (883)
"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-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, (332)
"Everything was outstanding!"
United States
Caroline E.
The price is P5,931
P6,465 total
includes taxes & fees
Dec 19 - Dec 20
My Place Hotel-Randolph VT
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (173)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is P9,658
P12,097 total
includes taxes & fees
Dec 1 - Dec 2
Mountain Meadows Lodge
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (558)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is P7,048
P7,752 total
includes taxes & fees
Nov 19 - Nov 20
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, (944)
"Excellent hotel. "
United States
Kristan
The price is P6,749
P7,795 total
includes taxes & fees
Nov 26 - Nov 27
The Mountain Inn at Killington
Front of property
The Vermont Inn

The Vermont Inn

3.0 star property
Rutland
9.2 out of 10, Wonderful, (413)
"Our room was clean and the bed was very comfortable. The Inn is for sale... which could explain the needed updates. I wish I could buy it! 🤗 We would stay here again. "
United States
Jodie
The price is P11,959
P13,035 total
includes taxes & fees
Nov 19 - Nov 20
The Vermont Inn
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)
"We love it here."
United States
Vanessa L
The price is P8,649
P9,514 total
includes taxes & fees
Dec 1 - Dec 2
Killington Mountain Lodge, Tapestry Collection by Hilton
Fireplace
Summit Lodge

Summit Lodge

3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"When we first arrived it felt really old and I was wondering what I had booked. Then, the place grew on me as I explored the hotel. I could see this as being really fun in the winter and with a group."
United States
Wendy
The price is P10,235
P11,259 total
includes taxes & fees
Dec 17 - Dec 18
Summit Lodge
Front of property
Cortina Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (640)
"location is excellent. As this is obviously an abandoned Holiday Inn, hopefully it is a renovation in progress."
United States
DICK
The price is P5,834
P6,417 total
includes taxes & fees
Nov 19 - Nov 20
Cortina Inn
Front of property
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 P17,383
P18,948 total
includes taxes & fees
Nov 19 - Nov 20
The Mountain Top Inn & Resort
Terrace/patio
On The River Inn

On The River Inn

4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1004)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is P13,965
P17,523 total
includes taxes & fees
Nov 22 - Nov 23
On The River Inn
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, (1001)
"Was perfect for our one night stay "
United Kingdom
Ian
The price is P6,205
P6,825 total
includes taxes & fees
Nov 19 - Nov 20
North Star Lodge and Resort
Front of property
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (975)
"This is a great place to stay. Attentive staff, easy parking, lots of options on the continental breakfast. "
United States
Lana
The price is P5,256
P5,781 total
includes taxes & fees
Nov 19 - Nov 20
Mountain Sports Inn
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"Newly renovated; clean and yet pet friendly. Waffles and hard boiled eggs for breakfast."
Lawrence 1-night trip
Posted 3 days ago
Days Inn by Wyndham Rutland/Killington Area

More cheap stays in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is P6,862 per night from Dec 10 to Dec 11
P6,862
P7,548 total
Dec 10 - Dec 11
includes taxes & fees
8/10 Very Good! (1,001 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.
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.
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 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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