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

Find Hotels with Bars in Pittsfield, VT

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with Bars

Tonight
Sep 18 - Sep 19
Tomorrow
Sep 19 - Sep 20
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Pittsfield hotels with a bar

1. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Corey
NT$4,420
NT$4,862 total
includes taxes & fees
Sep 21 - Sep 22
North Star Lodge and Resort

2. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
caroline
NT$5,762
NT$7,136 total
includes taxes & fees
Sep 21 - Sep 22
Mountain Meadows Lodge

3. Snowed Inn

Snowed Inn
Killington
United States
Brendan
NT$4,082
NT$4,940 total
includes taxes & fees
Sep 20 - Sep 21
Snowed Inn

4. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Kristen
NT$8,786
NT$9,577 total
includes taxes & fees
Sep 22 - Sep 23
The Mountain Top Inn & Resort

5. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Christopher
NT$4,277
NT$4,940 total
includes taxes & fees
Oct 18 - Oct 19
The Mountain Inn at Killington

6. Brandon Inn

Brandon Inn
Brandon
Canada
Sharon
NT$4,809
NT$5,290 total
includes taxes & fees
Sep 20 - Sep 21
Brandon Inn

7. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Andrew C
NT$4,390
NT$4,829 total
includes taxes & fees
Sep 27 - Sep 28
Comfort Inn Rutland - Killington

8. Killington Grand Hotel

Killington Grand Hotel
Base Area
United States
Amanda
NT$7,406
NT$8,687 total
includes taxes & fees
Oct 18 - Oct 19
Killington Grand Hotel

9. Inn at Neshobe River

Inn at Neshobe River
Brandon
United States
Keith
NT$5,566
NT$6,123 total
includes taxes & fees
Sep 20 - Sep 21
Inn at Neshobe River

10. The Lilac Inn

The Lilac Inn
Brandon
United States
Kymberly
NT$7,602
NT$8,362 total
includes taxes & fees
Sep 20 - Sep 21
The Lilac Inn
View all properties

Top Pittsfield Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
Laura 1-night trip
Posted 9 hours ago
The Jackson
Mountain Meadows Lodge

Mountain Meadows Lodge

8/10 Good
"The property is very comfortable with beautiful view of the lake. The evening bon fire proved to be a way to meet fellow travelers. There are many public rooms to keep you engaged. Site manager is very helpful and friendly."
Elena Viviana 1-night trip
Posted 14 hours ago
Mountain Meadows Lodge
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

8/10 Good
"Room was clean. Parking was easy. Breakfast was ok."
Jeffrey 1-night trip
Posted 17 hours ago
Days Inn by Wyndham Rutland/Killington Area
Woodstock Inn & Resort

Woodstock Inn & Resort

8/10 Good
"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."
Erin 3-night trip
Posted 18 hours ago
Woodstock Inn & Resort
On The River Inn

On The River Inn

8/10 Good
"Housekeeping was a bit lax. No tissues and only one hand towel. The rest of the Inn was great!"
Marion 1-night trip
Posted 1 day ago
On The River Inn
The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Stay was great, they have bike lockers to keep bikes at night super close to Killington lifts"
Christopher 1-night trip
Posted 2 days ago
The Mountain Inn at Killington
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"We loved the heated pool! Front desk staff were very helpful. Our room was clean and very basic. Our room was quiet. Would stay here again."
Lorraine 1-night trip
Posted 4 days ago
North Star Lodge and Resort
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good
"Stayed here because of the hot tub!!! Love that it was open until 11pm but wished it was open by like 8 am so we could have used it before we started our day !!"
Angie 2-night trip
Posted 4 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"Very good staff"
Nikhil 1-night trip
Posted 5 days ago
Courtyard Middlebury

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield features 40 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: The Mountain Inn at Killington: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Woodstock Inn & Resort: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Killington Mountain Lodge, Tapestry Collection by Hilton: B&B with restaurant. Enjoy the bar, free WiFi, and free parking. My Place Hotel-Randolph VT: Enjoy the bar, free breakfast, and sauna. Emrose Luxury Cabins: Hotel 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.

Explore a world of travel with Expedia