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

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Check availability on Pittsfield Hotels with Bars

Our top choices for Pittsfield hotels with a bar

Terrace/patio

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (8 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is AED 571
AED 622 total
includes taxes & fees
19 Jul - 20 Jul
Green Trails Inn
Exterior

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 AED 643
AED 707 total
includes taxes & fees
15 Jul - 16 Jul
Inn at Neshobe River
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, (1,014 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is AED 493
AED 569 total
includes taxes & fees
20 Jul - 21 Jul
The Mountain Inn at Killington
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (294 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is AED 711
AED 782 total
includes taxes & fees
15 Jul - 16 Jul
The Jackson
Exterior

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
9.0 out of 10, Wonderful, (581 reviews)
"This was a great hotel. I would definitely stay there again. Highly recommended."
United States
Thomas
The price is AED 559
AED 615 total
includes taxes & fees
22 Jul - 23 Jul
Courtyard Middlebury
Lobby

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.2 out of 10, Very Good, (1,007 reviews)
"very nice stay, very clean, staff very helpful"
United States
Mancione
The price is AED 426
AED 469 total
includes taxes & fees
22 Jul - 23 Jul
Comfort Inn Rutland - Killington
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (399 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is AED 470
AED 569 total
includes taxes & fees
15 Jul - 16 Jul
Snowed Inn
Fireplace

North Star Lodge and Resort

North Star Lodge and Resort
2.0 star property
Killington
8.8 out of 10, Excellent, (1,005 reviews)
"It was a very nice and comfortable stay Lee at the front desk was extremely"
United States
shaya
The price is AED 455
AED 500 total
includes taxes & fees
29 Jul - 30 Jul
North Star Lodge and Resort
Lake view

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.6 out of 10, Exceptional, (241 reviews)
"Great property for a nice getaway, plenty of amenities and the staff is top notch. Highly recommend"
United States
Scott
The price is AED 595
AED 746 total
includes taxes & fees
9 Aug - 10 Aug
Mountain Meadows Lodge
Front of property

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (656 reviews)
"Wonderful hosts, nice historic inn in quaint town"
United States
Katherine
The price is AED 532
AED 585 total
includes taxes & fees
22 Jul - 23 Jul
Brandon 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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Top Pittsfield Hotel Reviews

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Way better than most ski resort rooms."
Jim 2-night trip
Posted 6 hours ago
North Star Lodge and Resort

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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 area home - 4-seasons, hot tub and A/C: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Killington Mountain Lodge, Tapestry Collection by Hilton: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Woodstock Inn & Resort: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. The Mountain Inn at Killington: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. On The River Inn: Enjoy the bar, free breakfast, and sauna.
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.