Search Hotels with a Bar in Pittsfield

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Check availability on Pittsfield Hotels with a Bar

Our top choices for Pittsfield hotels with a bar

Exterior
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
2.5 star property
Rutland
8.0 out of 10, Very good, (1005)
"Clean rooms and polite workers. Try to stay there every time we go to Vermont."
United States
Michael
The price is 3.470.163 ₫
3.817.180 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Comfort Inn Rutland - Killington
Exterior
Courtyard Middlebury

Courtyard Middlebury

Courtyard Middlebury
3.0 star property
Middlebury
8.8 out of 10, Excellent, (544)
"Great hotel, fairly centered , great staff!"
United States
Angelo
The price is 2.888.071 ₫
3.176.878 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard Middlebury
Exterior
Brandon Inn

Brandon Inn

Brandon Inn
3.0 star property
Brandon
8.8 out of 10, Excellent, (566)
"Enjoyed our stay at the Brandon Inn very much!"
United States
Lesley
The price is 3.146.915 ₫
3.461.606 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Brandon Inn
Lake view
Mountain Meadows Lodge

Mountain Meadows Lodge

Mountain Meadows Lodge
3.5 star property
Killington
9.4 out of 10, Exceptional, (180)
"All round fantastic place to stay "
United Kingdom
Stephen
The price is 5.765.607 ₫
7.000.643 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mountain Meadows Lodge
Terrace/patio
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)
"This place was charming!! Enjoyed everything about it and so much to do right there in the inn."
United States
Ross
The price is 5.078.216 ₫
6.550.899 ₫ total
includes taxes & fees
22 Dec - 23 Dec
On The River Inn
Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets
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, (1003)
"Spotless room also very accommodating and friendly! Loved our short stay!"
United States
Candace
North Star Lodge and Resort
Front of property
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
Breakfast and dinner served
The Mountain Inn at Killington

The Mountain Inn at Killington

The Mountain Inn at Killington
2.5 star property
Killington
9.2 out of 10, Wonderful, (961)
"Great place to stay!"
United States
Stephen
The price is 5.902.570 ₫
6.817.587 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Mountain Inn at Killington
Fireplace
Summit Lodge

Summit Lodge

Summit Lodge
3.0 star property
Killington
8.6 out of 10, Excellent, (397)
"The staff was really great and helpful. There are a number of very cool public spaces to enjoy"
United States
George
The price is 4.570.394 ₫
5.027.433 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Summit Lodge
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (373)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
The price is 6.212.263 ₫
7.516.812 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Snowed 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

Cortina Inn

Cortina Inn

10/10 Excellent
"I am so happy with the service "
Sagrario 1-night trip
Posted 6 days ago
Cortina Inn

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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 an evening cocktail after exploring the city. While you're in the area, you can check out Killington Resort.
What is there to do in Pittsfield?
Consider a visit to Killington Resort, Gifford Woods State Park and Pico Mountain at Killington Ski Resort, and then find a cosy 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 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.
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 centre. 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, consider renting a car to explore more sights.