Find hotels in Pittsfield, VT from Rp1.806.715

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23 Dec - 24 Dec
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26 Dec - 28 Dec
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2 Jan - 4 Jan

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Our top choices for Pittsfield hotels

House, 4 Bedrooms | Exterior
The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home

The Getaway 4 Bedroom Home
3.0 star property
Pittsfield
The Getaway 4 Bedroom Home
Property grounds
The Shire Woodstock

The Shire Woodstock

The Shire Woodstock
3.0 star property
Woodstock
8.8 out of 10, Excellent, (893)
"Wonderful place to stay!"
United States
Robin
The Shire Woodstock
Restaurant
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (257)
"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, (1002)
"Rearaurant staff was top notch. "
United States
Daniel
The price is Rp5.452.525
Rp6.612.990 total
includes taxes & fees
29 Dec - 30 Dec
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, (329)
"Nice place to stay. Would stay there again & recommend it to friends and family "
United States
Deborah
Kedron Valley Inn
Deluxe Suite | Private kitchen | Mini-fridge, microwave, coffee/tea maker, freezer
Sleep Woodstock Motel

Sleep Woodstock Motel

Sleep Woodstock Motel
2.0 star property
Woodstock
9.6 out of 10, Exceptional, (549)
"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 Rp1.311.961
Rp2.491.720 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sleep Woodstock Motel
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
The price is Rp5.351.863
Rp6.625.237 total
includes taxes & fees
19 Jan - 20 Jan 2026
Woodstock Inn & Resort
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (183)
"Staff was amazing! They made the stay even better with their hospitality and overall service. I recommend this Lodge to anyone looking to go to Killington who wants a fun and relaxing stay. "
United States
Jaden
The price is Rp3.666.575
Rp4.451.983 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge
Interior
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (51)
"Charming bed and breakfast"
United States
Nicholas
The price is Rp3.109.135
Rp3.420.183 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Vesper
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
The price is Rp1.845.470
Rp2.085.381 total
includes taxes & fees
11 Jan - 12 Jan 2026
Mountain Valley Retreat
Interior
Turn of River Lodge

Turn of River Lodge

Turn of River Lodge
2.5 star property
Killington
8.8 out of 10, Excellent, (270)
"We enjoyed our stay. Close proximity to a lot of things to see and do. "
United States
Linda
The price is Rp1.928.093
Rp2.120.885 total
includes taxes & fees
4 Jan - 5 Jan 2026
Turn of River Lodge
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, (1001)
"Wonderful experience definitely would stay again."
United States
Ariel
The price is Rp3.150.385
Rp3.465.423 total
includes taxes & fees
21 Jan - 22 Jan 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (398)
"The staff was really great and helpful. There are a number of very cool public spaces to enjoy"
United States
George
The price is Rp2.909.475
Rp3.200.422 total
includes taxes & fees
4 Jan - 5 Jan 2026
Summit Lodge
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)
"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 Rp4.170.750
Rp4.587.824 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stay At Jimmy's
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, (1000)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (374)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is Rp3.961.050
Rp4.792.853 total
includes taxes & fees
6 Jan - 7 Jan 2026
Snowed Inn
Lounge
Greenbrier Inn

Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (646)
"It was a very quaint inn in a gorgeous location."
United States
ELIZABETH
Greenbrier Inn
Exterior
Après Inn Killington

Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (164)
"Wonderful location, beautiful renovations, friendly staff "
United States
Robyn
The price is Rp3.241.316
Rp3.565.448 total
includes taxes & fees
13 Jan - 14 Jan 2026
Après Inn Killington
Premium Suite, Multiple Beds | Balcony
Mountain Sports Inn

Mountain Sports Inn

Mountain Sports Inn
2.0 star property
The Woods
8.8 out of 10, Excellent, (987)
"Staff was great and breakfast was excellent "
United States
Bruce
The price is Rp2.160.750
Rp2.376.825 total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Sports Inn
Exterior
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is Rp4.889.824
Rp5.329.908 total
includes taxes & fees
5 Jan - 6 Jan 2026
Echo Lake 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

The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

10/10 Excellent
"Absolutely wonderful! The hotel and staff were great. We deeply appreciated the upgrade! No one wanted to leave. "
Wendy 1-night trip
Posted 1 month ago
The Mountain Top Inn & Resort

More cheap stays in Pittsfield

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2440 Vermont 66 Randolph Center VT
The price is Rp1.698.672 per night from 18 Jan to 19 Jan
Rp1.698.672
Rp1.851.552 total
18 Jan - 19 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (346 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 The Mountain Inn at 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, 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?
The Mountain Inn at Killington: Hotel, 1-minute walk from Killington Resort. Offers daily, an outdoor pool and free self parking. Woodstock Inn & Resort and North Star Lodge and 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 42 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.