Find Hotels with Bars in West Stockbridge, MA

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Check availability on West Stockbridge Hotels with Bars

Top West Stockbridge Hotels with Bars

Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (120)
"Great staff. Quiet.. and an excellent chef! Unique property and well worth it!"
Gedney Farm
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (86)
"Beautiful room and property. Perfect weekend getaway!"
The price is AED 1,065
AED 1,285 total
includes taxes & fees
16 Jul - 17 Jul
The Old Inn On The Green
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (672)
"We love this place. It's a wonderful location in the Berkshires, easy to get to all of the surrounding towns and attractions. The amenities are awesome, the units are spotless, and the service is friendly and prompt. Have stayed twice and cannot wait to return again!"
The price is AED 512
AED 624 total
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is AED 791
AED 883 total
includes taxes & fees
27 Jul - 28 Jul
Hilton Garden Inn Lenox Pittsfield
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (743)
"Great boutique hotel"
The price is AED 694
AED 775 total
includes taxes & fees
21 Jul - 22 Jul
Hotel On North
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1012)
"Great service and a wonderful place to stay"
The price is AED 465
AED 520 total
includes taxes & fees
24 Jul - 25 Jul
The Yankee, Trademark Collection by Wyndham
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (821)
"Very convenient location, downtown, short drive to local attractions "
The price is AED 422
AED 472 total
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hampton Terrace Inn
Exterior

Hampton Terrace Inn

4.0 star property
9.0 out of 10, Wonderful, (42)
"Beautiful historic house in a great location. Responsive owner. Great visit!"
The price is AED 1,289
AED 1,440 total
includes taxes & fees
14 Jul - 15 Jul
Hampton Terrace Inn
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (632)
"Great place stay after an evening at Tanglewood!"
The price is AED 1,484
AED 1,658 total
includes taxes & fees
25 Jul - 26 Jul
Berkshires Untold
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (564)
"The hotel is very clean, well-managed, and quiet, and it's conveniently located near Tanglewood and other attractions. The room is clean, and the staff are all extremely kind and attentive to our needs (special thanks to Tapan!) We will definitely be coming back!"
The price is AED 841
AED 940 total
includes taxes & fees
24 Jul - 25 Jul
Courtyard by Marriott Lenox Berkshires
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.

Frequently asked questions

Searching for hotels with bars in West Stockbridge?
West Stockbridge features 33 properties to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you're here, consider a visit to Stockbridge Bowl and Charles H. Baldwin & Sons.
What are the best hotels with bars in West Stockbridge?
Below are some of top hotels with bars in and around West Stockbridge: Pleasant Valley Motel West Stockbridge: Enjoy the poolside bar, 2 outdoor pools, and WiFi. FairBridge Inn Express: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Vacation Village in the Berkshires: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Howard Johnson by Wyndham Lenox: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Quality Inn: Enjoy the bar, free breakfast, and free WiFi.
What is there to do in West Stockbridge?
In the area, you can visit Berkshire Botanical Garden, Tanglewood Music Center, and Norman Rockwell Museum, then find a cozy spot for a nightcap. Other places to see include Stockbridge Bowl and Charles H. Baldwin & Sons. West Stockbridge is known for its restaurants.
When is the best time to visit West Stockbridge?
Visiting local bars in West Stockbridge is better when you know what the weather holds. These temperatures and rainfall averages can help you choose the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to West Stockbridge and around the area?
You might want to make the most of these transportation options in and around West Stockbridge: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 7.4 mi (11.9 km) away from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 17.8 mi (28.7 km) away. If you'd like to explore around the area, you may want a rental car for your journey.