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
7 Sep - 8 Sep
Tomorrow
8 Sep - 9 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Pittsfield hotels with a bar

Lake view
Lobby lounge
Exterior
Reception

1. Mountain Meadows Lodge

Mountain Meadows Lodge
Killington
United States
Brian
AED 500
AED 642 total
includes taxes & fees
17 Sep - 18 Sep
Mountain Meadows Lodge
Breakfast and dinner served
Superior Double Queen with Balcony | In-room safe, blackout drapes, WiFi (free), individually decorated
Breakfast and dinner served
Outdoor pool, a heated pool

2. The Mountain Inn at Killington

The Mountain Inn at Killington
Killington
United States
Allison
AED 410
AED 474 total
includes taxes & fees
9 Sep - 10 Sep
The Mountain Inn at Killington
Fireplace
Exterior
Snow and ski sports
Restaurant

3. North Star Lodge and Resort

North Star Lodge and Resort
Killington
United States
Corey
AED 509
AED 560 total
includes taxes & fees
9 Sep - 10 Sep
North Star Lodge and Resort
Front of property
Lobby sitting area
Dining room
Reception

4. Snowed Inn

Snowed Inn
Killington
United States
James
AED 466
AED 564 total
includes taxes & fees
9 Sep - 10 Sep
Snowed Inn
The Jewel | Living area | TV
The Jewel | Laptop workspace, iron/ironing board, individually decorated
Campion | Living area | TV
The Jewel | Living room | TV

5. The Mountain Top Inn & Resort

The Mountain Top Inn & Resort
Chittenden
United States
Kristen
AED 1,015
AED 1,106 total
includes taxes & fees
9 Sep - 10 Sep
The Mountain Top Inn & Resort
Fireplace
Indoor spa tub
Outdoor wedding area
Poolside bar

6. Summit Lodge

Summit Lodge
Killington
United States
Alex
AED 534
AED 679 total
includes taxes & fees
12 Sep - 13 Sep
Summit Lodge
Lobby
Dinner served
Lobby
Indoor pool

7. Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington
Rutland
United States
Andrew C
AED 520
AED 572 total
includes taxes & fees
10 Sep - 11 Sep
Comfort Inn Rutland - Killington
Front of property
Exterior
Front of property
Exterior

8. Brandon Inn

Brandon Inn
Brandon
Canada
Michael
AED 407
AED 448 total
includes taxes & fees
10 Sep - 11 Sep
Brandon Inn
Exterior
Lobby
Property entrance
Business center

9. Killington Grand Hotel

Killington Grand Hotel
Base Area
United States
Amanda
AED 853
AED 1,000 total
includes taxes & fees
9 Sep - 10 Sep
Killington Grand Hotel
Exterior
Restaurant
The Trillium Room | 1 bedroom, iron/ironing board, WiFi (free)
Exterior

10. Inn at Neshobe River

Inn at Neshobe River
Brandon
United States
Keith
AED 643
AED 707 total
includes taxes & fees
14 Sep - 15 Sep
Inn at Neshobe River
View all properties

Top Pittsfield Hotel Reviews

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Learning about the family running the place made us feel more at home. Snacks always available was a plus."
Nancy 4-night trip
Posted 4 hours ago
Mountain Meadows Lodge
Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Beautiful property, really special! Easy walk to shops."
crystal 1-night trip
Posted 6 hours ago
Woodstock Inn & Resort
Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"N/a"
Surbhi 1-night trip
Posted 20 hours ago
Mountain Sports Inn
The Jackson

The Jackson

10/10 Excellent
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Vicki 1-night trip
Posted 1 day ago
The Jackson
Hampton Inn Rutland

Hampton Inn Rutland

8/10 Good
"Most of the staff at the front desk needs to work on their people skills big time!!"
Kasey 4-night trip
Posted 1 day ago
Hampton Inn Rutland
On The River Inn

On The River Inn

10/10 Excellent
"Very nice. Breakfast is just an ordinary meal buffet."
Orrin 1-night trip
Posted 2 days ago
On The River Inn
North Star Lodge and Resort

North Star Lodge and Resort

8/10 Good
"Room alittle dates. Some updating should be done throughout. But all around nice place."
Tanya 3-night trip
Posted 6 days ago
North Star Lodge and Resort
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"A great place to stay when you’re visiting Killington!"
Mason 3-night trip
Posted 7 days ago
Killington Mountain Lodge, Tapestry Collection by Hilton
Courtyard Middlebury

Courtyard Middlebury

10/10 Excellent
"It was a very convenient location. There is a restaurant/bar, which was nice. The woman at the desk was incredibly friendly and helpful. We were very pleased with our stay and would stay there again."
Nancy 2-night trip
Posted 9 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: Killington area home - 4-seasons, hot tub and A/C: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. Comfort Inn Rutland - Killington: Hotel with restaurant. Enjoy the bar, free breakfast, and free WiFi. The Mountain Inn at Killington: Resort with 4 restaurants. Enjoy the 2 bars, free WiFi, and free valet parking. Woodstock Inn & Resort: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Emrose Luxury Cabins: Enjoy the bar, free breakfast, and sauna.
What is there to do in Pittsfield?
Consider a visit to Liberty Hill Farm, Green Mountain National Golf Course, and Gifford Woods State Park, 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.