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

Exterior

Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (337 reviews)
"I love staying at the Inn when I come to Vermont to see my friends compete at Green Mountain Horse Association. Cozy place."
United States
Marylynn
The price is AED 969
AED 1,065 total
includes taxes & fees
22 Jul - 23 Jul
Kedron Valley Inn
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (591 reviews)
"As always - best hotel in Vermont."
United States
ben
The price is AED 1,833
AED 2,178 total
includes taxes & fees
20 Aug - 21 Aug
Woodstock Inn & Resort
Hallway

On The River Inn

On The River Inn
4.0 star property
West Woodstock
9.4 out of 10, Exceptional, (1,003 reviews)
"convenient location with very comfortable accommodations"
United States
Tonine
The price is AED 888
AED 1,057 total
includes taxes & fees
6 Aug - 7 Aug
On The River Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (296 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is AED 592
AED 651 total
includes taxes & fees
28 Jul - 29 Jul
The Jackson
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is AED 770
AED 840 total
includes taxes & fees
22 Jul - 23 Jul
Echo Lake Inn
Terrace/patio

Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Historical charm combined with Immaculate style—- killer food hospitality highly recommend this place—- so wonderful"
United States
Christine
The price is AED 565
AED 616 total
includes taxes & fees
3 Aug - 4 Aug
Green Trails Inn
Exterior

Killington Grand Hotel

Killington Grand Hotel
3.5 star property
Base Area
9.0 out of 10, Wonderful, (216 reviews)
"Amazing place!"
United States
Sheryl
The price is AED 853
AED 1,000 total
includes taxes & fees
22 Jul - 23 Jul
Killington Grand Hotel
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (400 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
The price is AED 470
AED 569 total
includes taxes & fees
22 Jul - 23 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, (1,002 reviews)
"It was a very nice and comfortable stay Lee at the front desk was extremely"
United States
shaya
The price is AED 505
AED 556 total
includes taxes & fees
22 Jul - 23 Jul
North Star Lodge and Resort
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, (1,004 reviews)
"Great place to stay with the best staff!"
United States
Travis
The price is AED 493
AED 569 total
includes taxes & fees
27 Jul - 28 Jul
The Mountain Inn at Killington
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"The best Days Inn breakfast I have ever seen. Nice variety of hot and cold choices."
William 1-night trip
Posted 3 hours ago
Days Inn by Wyndham Rutland/Killington Area

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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. 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. Killington Mountain Lodge, Tapestry Collection by Hilton: B&B with restaurant. Enjoy the bar, free WiFi, and free parking.
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.