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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 AU$1,543
includes taxes & fees
18 Dec - 19 Dec
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, (1000)
"We like that there are rooms available with a good size kitchen, living area and dining room."
United States
Amy
Travelling with friends
The price is AU$268
includes taxes & fees
11 Dec - 12 Dec
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, (1002)
"The best part about the stay was the shower!"
United States
Donna
Travelling with partner
The price is AU$194
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn 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, (1004)
"The staff was fantastic the room was clean"
United States
Edward
Travelling with family
The price is AU$197
includes taxes & fees
7 Dec - 8 Dec
Days Inn by Wyndham Rutland/Killington Area
Exterior
Hampton Inn Rutland

Hampton Inn Rutland

2.5 star property
Rutland
9.0 out of 10, Wonderful, (966)
"Decent breakfast, clean hotel, friendly staff, good location to venture out and explore other areas."
United States
Gladys
Travelling for leisure
The price is AU$231
includes taxes & fees
11 Dec - 12 Dec
Hampton Inn Rutland
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Concierge was amazing and so helpful with movie tickets and dinner plans!"
United States
kathleen
Travelling with pet
The price is AU$631
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & Resort
Deluxe Suite
Sleep Woodstock Motel

Sleep Woodstock Motel

2.0 star property
Woodstock
9.6 out of 10, Exceptional, (547)
"The suite was lovely and spacious."
United States
Andrea
Travelling for leisure
The price is AU$248
includes taxes & fees
7 Dec - 8 Dec
Sleep Woodstock Motel
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, (339)
"Beautiful, clean new hotel with friendly staff."
United States
Teri
Travelling for leisure
The price is AU$164
includes taxes & fees
4 Jan - 5 Jan 2026
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, (415)
"Room was incredibly spacious, clean, and comfortable."
United States
Ann
Travelling with partner
The price is AU$334
includes taxes & fees
7 Dec - 8 Dec
The Vermont Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 star property
Killington
9.4 out of 10, Exceptional, (178)
"the bed was super comfortable"
United States
Leah
Travelling with friends
The price is AU$311
includes taxes & fees
7 Dec - 8 Dec
Mountain Meadows Lodge
Front of property
Cortina Inn

Cortina Inn

3.0 star property
Rutland
6.6 out of 10, (647)
"The room was nice and clean."
United States
Randy
The price is AU$165
includes taxes & fees
8 Dec - 9 Dec
Cortina Inn
Property grounds
The Shire Woodstock

The Shire Woodstock

3.0 star property
Woodstock
8.8 out of 10, Excellent, (887)
"Great location, clean rooms, and helpful staff"
United States
Jeffrey
The Shire Woodstock
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, (953)
"The staff was so welcoming and friendly, the rooms were immaculate and"
United States
Pearlie
The price is AU$329
includes taxes & fees
7 Dec - 8 Dec
The Mountain Inn at Killington
Fireplace
Summit Lodge

Summit Lodge

3.0 star property
Killington
8.6 out of 10, Excellent, (396)
"Plenty of things to do on the property after a good long day of skiing"
United States
Uri
Travelling for leisure
The price is AU$289
includes taxes & fees
17 Dec - 18 Dec
Summit 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)
"The room was above and beyond excellent."
United States
Martin
Travelling for leisure
The price is AU$244
includes taxes & fees
9 Dec - 10 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
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, (1001)
"the pool was clean and enjoyable"
United States
Samantha
Travelling for leisure
North Star Lodge and Resort
Exterior
Brandon Inn

Brandon Inn

3.0 star property
Brandon
8.8 out of 10, Excellent, (564)
"The bed was very comfortable."
United States
Stephen
The price is AU$185
includes taxes & fees
8 Dec - 9 Dec
Brandon Inn
Front of property
Mountain Sports Inn

Mountain Sports Inn

2.0 star property
The Woods
8.8 out of 10, Excellent, (979)
"our room was incredibly clean"
United States
Kristen
Travelling for leisure
The price is AU$181
includes taxes & fees
7 Dec - 8 Dec
Mountain Sports Inn
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, (95)
"Long View Barn: Pros: gorgeous views, nice cabin/house, very clean, fully stocked kitchen."
United States
Catherine
Travelling for leisure
The price is AU$536
includes taxes & fees
7 Dec - 8 Dec
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, (1010)
"The hotel is fab, really clean"
United Kingdom
Verena
Travelling for leisure
The price is AU$450
includes taxes & fees
6 Dec - 7 Dec
On The River 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.
See properties

Top Pittsfield Hotel Reviews

Recent Reviews in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"Everything was excellent"
John 1-night trip
Posted 3 days ago
Comfort Inn Rutland - Killington

More cheap accommodation in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

19 Allen St Rutland VT
The price is AU$194 per night from 10 Dec to 11 Dec
AU$194
10 Dec - 11 Dec
includes taxes & fees
8/10 Very Good! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Pittsfield?
Located 17.9 mi (28.9 km) from the heart of Pittsfield, Woodstock Inn & Resort 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 Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.
What are some of the best holiday rentals that Pittsfield has to offer?
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: This holiday home rental outside Pittsfield is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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?
Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Comfort Inn Rutland - Killington 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.

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