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

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Our top choices for Pittsfield hotels with a bar

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (576 reviews)
"Clean room, helpful staff, good restaurants, onsite guest laundry."
United States
Anne
The price is NT$4,571
NT$5,029 total
includes taxes & fees
Jul 26 - Jul 27
Courtyard Middlebury

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (1,002 reviews)
"Clean, comfortable and great location. Plus they have a hotel dog on staff!"
United States
Laura
The price is NT$4,859
NT$5,612 total
includes taxes & fees
Jul 12 - Jul 13
The Mountain Inn at Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very Good, (1,002 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is NT$4,258
NT$4,684 total
includes taxes & fees
Aug 2 - Aug 3
Comfort Inn Rutland - Killington

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (6 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is NT$5,398
NT$5,884 total
includes taxes & fees
Jul 20 - Jul 21
Green Trails Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (648 reviews)
"Spacious comfortable family suite. Convenient location, clean beautiful inn, great customer service."
United States
Eva
The price is NT$4,817
NT$5,299 total
includes taxes & fees
Jul 7 - Jul 8
Brandon Inn

Inn at Neshobe River

Inn at Neshobe River
3.0 star property
Brandon
9.6 out of 10, Exceptional, (18 reviews)
"Great little BAnd B just outside town. Shares property with a brewery and also offers a small food menu for dinner Fantastic view of the golf course 5 th hole Great hospitality and crazy good breakfast "
United States
Keith
The price is NT$5,591
NT$6,150 total
includes taxes & fees
Jul 6 - Jul 7
Inn at Neshobe River

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,001 reviews)
"Great pool, bar, & staff!"
United States
Patrick
The price is NT$4,393
NT$4,832 total
includes taxes & fees
Jul 19 - Jul 20
North Star Lodge and Resort

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (236 reviews)
"Beautiful couple for hosts and stunning location. Great breakfast and hot tub to relax after a long drive. Will come back to stay longer"
Canada
Tanuja
The price is NT$5,032
NT$6,334 total
includes taxes & fees
Jul 21 - Jul 22
Mountain Meadows Lodge

The Vermont Inn

The Vermont Inn
3.0 star property
Rutland
9.2 out of 10, Wonderful, (430 reviews)
"Clean, cozy, nice staff!"
United States
Mary
The price is NT$6,221
NT$6,781 total
includes taxes & fees
Jul 8 - Jul 9
The Vermont Inn

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,002 reviews)
"Beautiful place to stay"
United States
Jeff
The price is NT$7,156
NT$8,399 total
includes taxes & fees
Jul 19 - Jul 20
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.

Top Pittsfield Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield features 42 properties to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, you can check out Green Mountain National Forest and Roger Clark Memorial Central Library.
What are the best hotels with bars in Pittsfield?
Below are some of top hotels with bars in and around Pittsfield: Killington Mountain Lodge, Tapestry Collection by Hilton: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Woodstock Inn & Resort: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. The Mountain Inn at Killington: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. On The River Inn: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. My Place Hotel-Randolph VT: Enjoy the bar, free breakfast, and free WiFi.
What is there to do in Pittsfield?
Consider a visit to Green Mountain National Golf Course, Gifford Woods State Park, and Pico Mountain at Killington Ski Resort, and then find a cozy spot for a nightcap. Other places to see include Green Mountain National Forest and Roger Clark Memorial Central Library.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. 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.
How can I get to Pittsfield and around the area?
Here are some of your transportation choices in and around Pittsfield: Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) from the city center. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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