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Our top choices for Stockbridge hotels with a bar
1. The Red Lion Inn
The Red Lion Inn3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
8.8/10
Excellent
(1,006 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
Mallory
The price is NT$5,132
NT$5,132
NT$7,352 total
includes taxes & fees
Nov 8 - Nov 9
2. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,000 reviews)
9.2/10
Wonderful
(1,000 reviews)
"Nice place to stay"
"Nice place to stay"Michael
The price is NT$3,625
NT$3,625
NT$4,690 total
includes taxes & fees
Nov 5 - Nov 6
3. The Yankee Inn
The Yankee Inn2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
9.2/10
Wonderful
(1,013 reviews)
"The location was good for our trip."
"The location was good for our trip."Basil
The price is NT$3,747
NT$3,747
NT$4,186 total
includes taxes & fees
Nov 20 - Nov 21
4. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox Berkshires3.0 star property
Lenox
9.2 out of 10, Wonderful, (684 reviews)
9.2/10
Wonderful
(684 reviews)
"Great stay!"
"Great stay!"Vandhana
The price is NT$4,093
NT$4,093
NT$4,572 total
includes taxes & fees
Nov 8 - Nov 9
5. Berkshires Untold
Berkshires Untold3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,065 reviews)
9.0/10
Wonderful
(1,065 reviews)
"Very nice place beautiful view"
"Very nice place beautiful view"Brian
The price is NT$3,975
NT$3,975
NT$4,440 total
includes taxes & fees
Nov 29 - Nov 30
6. Hotel On North
Hotel On North3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (978 reviews)
9.6/10
Exceptional
(978 reviews)
"Very nice hotel"
"Very nice hotel"Philip
The price is NT$3,783
NT$3,783
NT$4,225 total
includes taxes & fees
Nov 30 - Dec 1
7. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
9.2/10
Wonderful
(716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
"Great place to stay. Great staff and convenient location. Nice restaurant as well."James
The price is NT$3,867
NT$3,867
NT$4,319 total
includes taxes & fees
Nov 15 - Nov 16
8. Element by Marriott Lenox Berkshires
Element by Marriott Lenox Berkshires3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
9.6/10
Exceptional
(51 reviews)
"Clean, spacious room
Accommodating staff especially Shawn and Jennifer at the front desk.
Very nice pool and gym
Definitely coming back"
"Clean, spacious room
Accommodating staff especially Shawn and Jennifer at the front desk.
Very nice pool and gym
Definitely coming back"Francis
The price is NT$4,399
NT$4,399
NT$4,913 total
includes taxes & fees
Nov 11 - Nov 12
9. The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
9.4/10
Exceptional
(1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
"Lovely room, comfortable bed and a nice breakfast."
judith
The price is NT$5,540
NT$5,540
NT$6,354 total
includes taxes & fees
Nov 8 - Nov 9
10. Hampton Terrace Inn
Hampton Terrace Inn4.0 star property
Lenox
9.0 out of 10, Wonderful, (45 reviews)
9.0/10
Wonderful
(45 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."Kathleen
The price is NT$7,491
NT$7,491
NT$8,367 total
includes taxes & fees
Nov 11 - Nov 12
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.
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.
Top Stockbridge Hotel Reviews
The Red Lion Inn
The Red Lion InnStockbridge
10/10 Excellent
This is a Classic Old Historic Inn full of Antiques, Art, & Character. The Restaurant & Music in the Basement is Very Good. Remember not to miss the Cozy Fire in the Winter or the Front Porch in the Summer.
This is a Classic Old Historic Inn full of Antiques, Art, & Character. The Restaurant & Music in the Basement is Very Good. Remember not to miss the Cozy Fire in the Winter or the Front Porch in the Summer.
Michael
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the BerkshiresSouth Lee
10/10 Excellent
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...
David
Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
10/10 Excellent
Room was so nice. Bed was comfortable. Overall glad we stayed here.
Room was so nice. Bed was comfortable. Overall glad we stayed here.
Alyssa
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The BerkshiresLenox
10/10 Excellent
VERY friendly staff and location for area attractions.
VERY friendly staff and location for area attractions.
Lawrence
The Yankee Inn
The Yankee InnLenox
10/10 Excellent
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!
Colleen
Brook Farm Inn
Brook Farm InnLenox
10/10 Excellent
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
We were very happy with our stay… Maureen was so hospitality and made sure all our needs were taken care of, from lending us an Apple plug, making dinner reservations for us to making sure we had all enough breakfast food. We love Lennox and would definitely want to stay at her place again, when we come back. Thank Maureen for the special time!
roberta
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
10/10 Excellent
The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was
The staff could not have been more helpful, great location and the facility extremely clean. We were shocked about how amazing this place was
t
Berkshires Untold
Berkshires UntoldLenox
10/10 Excellent
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free.
There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...
Jill
Prospect Berkshires
Prospect BerkshiresEgremont
10/10 Excellent
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
So fantastic!! The cabins are gorgeous and very well appointed. We are going back!
Emily
Hotel On North
Hotel On NorthPittsfield
10/10 Excellent
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...
Steve
Little Cat Lodge
Little Cat LodgeCopake Falls
10/10 Excellent
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
I didn't want to leave and wish I had time to stay longer. Room was exceptional. Staff was exceptional. A truly great stay.
Elisabeth
Gateways Inn & Restaurant
Gateways Inn & RestaurantLenox
10/10 Excellent
The inn is a wonderful and charming grand home in Lenox. The interior has warm furnishings and the staff went out of their way to make us feel welcome. Dinner was outstanding and the wine list had many examples of fine wines from Israel. Breakfast the next morning featured a sumptuous challah french toast souffle.
The inn is a wonderful and charming grand home in Lenox. The interior has warm furnishings and the staff went out of their way to make us feel welcome. Dinner was outstanding and the wine list had many examples of fine wines from Israel. Breakfast the next morning featured a sumptuous challah french toast souffle.
Richard
The Old Inn On The Green
The Old Inn On The GreenGreat Barrington
10/10 Excellent
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Truly enjoyed the stay. Peter and his staff were extremely helpful and hospitable.
Rishi
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
10/10 Excellent
One of the best hotel i been in my life. Everyone that works there is so friendly. From the front desk to the restaurant are amazing. The food is delicious and the pool is beautiful and the entire hotel is clean. I went from staying from one day to three days.
One of the best hotel i been in my life. Everyone that works there is so friendly. From the front desk to the restaurant are amazing. The food is delicious and the pool is beautiful and the entire hotel is clean. I went from staying from one day to three days.
Gipsy
Jiminy Peak Mountain Resort
Jiminy Peak Mountain ResortHancock
10/10 Excellent
Everything there was great except Christiansens taver. The service was ok but the food was terrible. I would not recommend this place for dining. I would go to McDonalds before I ate there again. We do however recommend Powder Hounds Tavern at the entrance, The service and the food were excellent and affordable.
Everything there was great except Christiansens taver. The service was ok but the food was terrible. I would not recommend this place for dining. I would go to McDonalds before I ate there again. We do however recommend Powder Hounds Tavern at the entrance, The service and the food were excellent and affordable.
Lloyd A.
Frequently Asked Questions
Searching for hotels with bars in Stockbridge?
Stockbridge offers 55 hotels and other accommodations to choose from, and likely many will have a bar where you can enjoy an evening cocktail after sightseeing. While you’re here, you can check out Naumkeag Museum and National Shrine of the Divine Mercy.
What are the best hotels with bars in Stockbridge?
Here are some favorite hotels with bars in and around Stockbridge: The Red Lion Inn: Hotel with 3 restaurants. Enjoy the bar, free WiFi, and free parking. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Enjoy the bar, free breakfast, and free WiFi. Vacation Village in the Berkshires: Lodge with restaurant. Enjoy the bar, free WiFi, and free parking. Berkshire Mountain Lodge: Enjoy the poolside bar, 2 outdoor pools, and WiFi. Quality Inn Great Barrington: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Stockbridge?
Consider a visit to Naumkeag Museum, National Shrine of the Divine Mercy, and Norman Rockwell Museum, and then find a cozy spot for a nightcap. Other places to see include Berkshire Botanical Garden and Stockbridge Bowl. Stockbridge is appreciated for its bars.
When is the best time to visit Stockbridge?
Visiting local bars in Stockbridge is more fun in good weather. These rainfall averages and temperatures can help you determine 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 Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Stockbridge and around the area?
Here are some of your transportation options in and around Stockbridge: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 9.6 mi (15.5 km) from the heart of the city. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.