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Our top choices for Pittsfield hotels

1. The Trailside Inn

The Trailside Inn
3.0 star property
North Sherburne
9.2 out of 10, Wonderful, (167 reviews)
"Such a welcoming and friendly place for a stay"
United States
Marc
The price is ¥25,451
¥27,996 total
includes taxes & fees
Nov 30 - Dec 1
The Trailside Inn

2. Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (377 reviews)
"This place is awesome, Clean, beautiful, great location, great staff, super breakfast."
United States
Kathy
The price is ¥20,404
¥26,438 total
includes taxes & fees
Nov 15 - Nov 16
Mountain Meadows Lodge

3. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
3.5 star property
Chittenden
9.0 out of 10, Wonderful, (132 reviews)
"Oh wow!! I would stay here again tomorrow! Beautiful property, restaurant has amazing food and convenient location. We stayed in the Long View Barn, the 60 mile view was even more spectacular than we imagined!"
United States
Allison
The price is ¥32,546
¥35,475 total
includes taxes & fees
Nov 23 - Nov 24
The Mountain Top Inn & Resort

4. Greenbrier Inn

Greenbrier Inn
2.0 star property
Killington
9.4 out of 10, Exceptional, (706 reviews)
"Very friendly staff with easy check in and out. Breakfast was fast and convenient and great location!"
United States
Jeff
The price is ¥27,946
¥32,207 total
includes taxes & fees
Nov 19 - Nov 20
Greenbrier Inn

5. Mountain Sports Inn

Mountain Sports Inn
2.0 star property
Killington
8.8 out of 10, Excellent, (1,000 reviews)
"Would definitely stay again"
United States
Pamela
The price is ¥17,415
¥19,156 total
includes taxes & fees
Nov 22 - Nov 23
Mountain Sports Inn

6. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (439 reviews)
"It was a fantastic stay and all that we wanted in a charming inn on the mountain."
United States
Marleen
The price is ¥27,640
¥33,444 total
includes taxes & fees
Dec 1 - Dec 2
Snowed Inn

7. North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.6 out of 10, Excellent, (1,002 reviews)
"Perfect service and friendly staff!!"
United States
Toghrul
The price is ¥18,872
¥20,759 total
includes taxes & fees
Nov 22 - Nov 23
North Star Lodge and Resort

8. Killington Haus

Killington Haus
2.0 star property
Killington
9.2 out of 10, Wonderful, (72 reviews)
"Clean room, clean place, warm and cozy inside. A great place to stay in Killington!"
United States
Ivan
The price is ¥19,332
¥21,266 total
includes taxes & fees
Nov 14 - Nov 15
Killington Haus

9. The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,006 reviews)
"Great hotel!"
United States
Petra
The price is ¥18,869
¥21,795 total
includes taxes & fees
Nov 15 - Nov 16
The Mountain Inn at Killington

10. Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington
2.5 star property
Rutland
8.8 out of 10, Excellent, (1,000 reviews)
"clean, staff welcoming, and breakfast was solid."
United States
Bryce
The price is ¥25,741
¥28,316 total
includes taxes & fees
Nov 19 - Nov 20
Best Western Inn & Suites Rutland-Killington

11. Après Inn Killington

Après Inn Killington
2.0 star property
Killington
9.4 out of 10, Exceptional, (208 reviews)
"modern and clean, wifi worked great"
United States
Kylie
The price is ¥22,048
¥24,253 total
includes taxes & fees
Nov 19 - Nov 20
Après Inn Killington

12. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1,000 reviews)
"This was a good hotel for a decent price."
United States
Leila
The price is ¥18,877
¥20,764 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn Rutland - Killington

13. Hampton Inn Rutland

Hampton Inn Rutland
2.5 star property
Rutland
9.0 out of 10, Wonderful, (1,000 reviews)
"The fitness room was very good, lots of towels, access to television channels, the equipment was in super shape."
Canada
Stewart
The price is ¥22,000
¥24,200 total
includes taxes & fees
Dec 13 - Dec 14
Hampton Inn Rutland

14. 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, (1,000 reviews)
"Great hotel with an amazing staff."
United States
Richard
The price is ¥18,605
¥20,465 total
includes taxes & fees
Nov 23 - Nov 24
Killington Mountain Lodge, Tapestry Collection by Hilton

15. Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area
2.5 star property
Rutland
7.0 out of 10, Good, (1,004 reviews)
"Nice place good breakfast"
Canada
Jim
The price is ¥18,877
¥20,765 total
includes taxes & fees
Nov 16 - Nov 17
Days Inn by Wyndham Rutland/Killington Area

16. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (342 reviews)
"Excellent stay"
United Kingdom
Richard
The price is ¥19,684
¥21,652 total
includes taxes & fees
Dec 1 - Dec 2
The Jackson

17. Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (740 reviews)
"We were pleasantly surprised by how charming this place was. Clean room, incredibly friendly staff. Will definitely come back next time we're in VT."
United States
Ha
The price is ¥20,635
¥22,698 total
includes taxes & fees
Nov 16 - Nov 17
Brandon Inn

18. On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.2 out of 10, Wonderful, (1,008 reviews)
"Great place would stay again"
United States
Joseph
The price is ¥20,831
¥26,108 total
includes taxes & fees
Dec 6 - Dec 7
On The River Inn

19. My Place Hotel-Randolph VT

My Place Hotel-Randolph VT
2.0 star property
Randolph Center
9.4 out of 10, Exceptional, (646 reviews)
"Just passing through and was a great place to stay.."
United States
Debra
The price is ¥15,659
¥17,069 total
includes taxes & fees
Dec 7 - Dec 8
My Place Hotel-Randolph VT

20. Emrose Luxury Cabins

Emrose Luxury Cabins
2.0 star property
Brandon
8.8 out of 10, Excellent, (210 reviews)
"It’s was a really sweet place to spend a weekend getaway."
United States
Alexandra
The price is ¥25,902
¥29,269 total
includes taxes & fees
Nov 30 - Dec 1
Emrose Luxury Cabins
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.

Stay near popular Pittsfield attractions

Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

A lake surrounded by autumn-colored trees and a rocky shoreline.

Top Pittsfield Hotel Reviews

Frequently Asked Questions

What's the top vacation rental in Pittsfield?

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.: You might like this vacation home rental near Pittsfield. It is located in a rural location and has a fireplace, a patio, and a barbecue grill 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 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, 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.

Where can I learn more about changing or cancelling my trip to Pittsfield?

To find more details about changing or cancelling your trip to Pittsfield, go to https://www.expedia.com/service/.

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?

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 Emrose Luxury Cabins are a couple of other choices with an onsite pool. View all hotels with pools in Pittsfield.

What's the best accommodation near Rutland Southern Vermont Regional Airport (RUT)?

Comfort Inn Trolley Square is one of the top choices for your stay and is a popular hotel, featuring free breakfast and an indoor pool. It's located 4.9 mi (7.8 km) from Rutland Southern Vermont Regional Airport. Other choices near the airport include Holiday Inn Rutland-Killington Area and Quality Inn Rutland.

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 34 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, Pittsfield Town Hall, and Roger Clark Memorial Central Library. You'll also find Green Mountain National Golf Course and Gifford Woods State Park 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.

Where is the best place to stay in Pittsfield?

Located 9.8 mi (15.8 km) from the heart of Pittsfield, The Mountain Inn at Killington is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Woodstock Inn & Resort and Killington Mountain Lodge, Tapestry Collection by Hilton. See all available top hotels, or vacation rentals in Pittsfield.

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