Find Winery Hotels in The Berkshires, MA

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Top The Berkshires Winery Hotels

The Barrington
4 out of 5
281 Main St., Level 3, Great Barrington, MA
4.8/5 Exceptional! (72 reviews)
"Delightfully welcoming"

Reviewed on Jun 15, 2021

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The Barrington
Shaker Mill Inn
2.5 out of 5
2 Oak Street, West Stockbridge, MA
The price is $145 per night from Nov 2 to Nov 2
4.8/5 Exceptional! (265 reviews)
"John was an excellent host. The room was amazing and very comfortable. The bed was very comfortable. It was a very relaxing stay and we wish we would have booked an extra day there to just relax and chill on our trip through New England."

Reviewed on Sep 29, 2021

Shaker Mill Inn
The Cornell Inn, Lenox
3 out of 5
203 Main St, Lenox, MA
The price is $200 per night from Nov 8 to Nov 8
4.6/5 Wonderful! (311 reviews)
"My wife and I just spent three wonderful days at the Cornell Inn. The decor is beautiful and unique. The breakfasts were delicious and creative. The staff was friendly, helpful and attentive. And the location is very convenient."

Reviewed on Oct 19, 2021

The Cornell Inn, Lenox
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Garden Gables Inn
4 out of 5
135 Main St, Lenox, MA
4.6/5 Wonderful! (55 reviews)
"This is a beautiful, charming, B&B in a great location in Lenox. The staff is absolutely wonderful. The breakfast is exceptional. I highly recommend the Garden Gables Inn."

Reviewed on Oct 20, 2021

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Garden Gables Inn
Birchwood Inn
3.5 out of 5
7 Hubbard Street, Lenox, MA
The price is $170 per night from Oct 27 to Oct 27
4.6/5 Wonderful! (78 reviews)
"Wonderful atmosphere and property history…close to other venues."

Reviewed on Oct 4, 2021

Birchwood Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is $127 per night from Nov 2 to Nov 2
4.5/5 Wonderful! (471 reviews)
"Very friendly staff and hotel was clean and quiet. Would recommend to anyone."

Reviewed on Oct 17, 2021

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Inn At Richmond
3 out of 5
802 State Road, Richmond, MA
4.5/5 Wonderful! (39 reviews)
Comfortable B&B near Lenox, Massachusetts
"Charming Revolutionary War era Bed and Breakfast on a sprawling horse farm, minutes from all cultural activities in Lenox. Room was comfortable, and the house is conducive to socializing with other guests."

Reviewed on Aug 13, 2018

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Inn At Richmond
The Old Inn On The Green
4 out of 5
134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
The price is $260 per night from Nov 2 to Nov 2
4.4/5 Wonderful! (52 reviews)
"Back in time in facility, awesomely relaxing environment amd area."

Reviewed on Oct 18, 2021

The Old Inn On The Green
Monument Mountain Motel
2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is $70 per night from Nov 1 to Nov 1
4.4/5 Excellent! (298 reviews)
"Good value for just an overnight stay. The desk clerk was very polite and helpful. Knowledgeable about the area. The room itself was fine, small but very clean. It didn't have a coffee pot, had a refrigerator but no freezer, kind of shabby worn loveseat but it was comfortable. Bed was very comfortable. ..."

Reviewed on Sep 28, 2021

Monument Mountain Motel
Kemble Inn
3.5 out of 5
2 Kemble Street, Lenox, MA
4.4/5 Excellent! (31 reviews)
"wonderfully restored old mansion. Rooms were charming... nicely designed. In fact the entire facility has been thoughtfully brought into today's design standards. Very accomodating staff... although many appeared to be a training mode. Need to improve the professionalism a bit. They have a new general ..."

Reviewed on Nov 2, 2019

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Kemble Inn
Yankee Inn
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $81 per night from Nov 9 to Nov 9
4.2/5 Excellent! (948 reviews)
"Beautiful room and friendly staff, only stayed for one night but it was great and we will be back!"

Reviewed on Oct 20, 2021

Yankee Inn
Gateways Inn & Restaurant
3 out of 5
51 Walker St, Lenox, MA
The price is $220 per night from Nov 1 to Nov 1
4.2/5 Very Good! (59 reviews)
"Comfortable, traditional inn with excellent service and restaurant. Facilities were clean and up to date. Walking distance to everything in town. Highly recommended."

Reviewed on Oct 4, 2021

Gateways Inn & Restaurant
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is $96 per night from Nov 2 to Nov 2
4.2/5 Very Good! (734 reviews)
"The refrigerator in our room wasn’t working. Noisy plumbing. Staff was friendly. Very clean property. Room was very comfy."

Reviewed on Oct 16, 2021

Best Western Plus Berkshire Hills Inn & Suites
Lantern House Motel
2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
The price is $65 per night from Nov 2 to Nov 2
4.1/5 Very Good! (433 reviews)
"Well maintained property, large clean rooms, vintage furnishings. Comfortable,quiet atmosphere right on the main route through town. Just a few minutes from the wonderful Norman Rockwell Museum, a must-see. Bakery next door, walking distance to shopping plaza with grocery store, Marshall's, McDonald's ..."

Reviewed on Oct 14, 2021

Lantern House Motel
Whistler's Inn Bed & Breakfast
3.5 out of 5
5 Greenwood Street, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $204 per night from Oct 25 to Oct 25
4/5 Very Good! (225 reviews)
"Inn has only open 3 weeks, musty terrible smells. Breakfast never provided and cold coffee. No tv or internet as advertised. Limited parking."

Reviewed on Aug 28, 2021

Whistler's Inn Bed & Breakfast
Days Inn by Wyndham Great Barrington
2 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is $67 per night from Nov 2 to Nov 2
3.8/5 Good! (728 reviews)
"A little challenge locating as pix shown is rear view not seen from Main St. # not shown. Too bad local business / restaurant info not available in lobby."

Reviewed on Oct 16, 2021

Days Inn by Wyndham Great Barrington
Chesapeake Inn of Lenox
3 out of 5
210 West Street, P.O. Box 1920, Lenox, MA
3.6/5 Good! (8 reviews)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"

Reviewed on Oct 14, 2019

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Chesapeake Inn of Lenox
Pleasant Valley Motel West Stockbridge
2 out of 5
42 Stockbridge Rd, West Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is $67 per night from Nov 1 to Nov 1
3.4/5 Good! (769 reviews)
"Super friendly staff and guests make this a chill basic motel in a great location. Great value."

Reviewed on Sep 16, 2021

Pleasant Valley Motel West Stockbridge
Knights Inn Lenox
1.5 out of 5
474 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is $50 per night from Nov 16 to Nov 16
2.9/5 (280 reviews)
"The room smelled musty, I believe it was a long time since your window was opened to ventilate the room. The bedding didn't have that freshly washed smell, either. It is definitely terrible for allergic people!"

Reviewed on May 24, 2021

Knights Inn Lenox
Wheatleigh
5 out of 5
11 Hawthorne Rd, Lenox, MA
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Wheatleigh
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Your Guide to The Berkshires Winery Hotels

If you are looking for a vacation where you spend time enjoying the finer things in life, then look no further than touring a wine region. The Berkshires is fast becoming a place where wine enthusiast try the latest styles, as well as those that are new to the greatest hits of the grape. The Berkshires offers the perfect starting point for you to check out all the characteristic of each variety and the traits that make this town worth visiting. But even if you are spending most of your days touring vineyards, you'll need a place to stay. Expedia has 844 hotels near wineries, making it easy to tour, toast, and take in everything in The Berkshires.

Wine Time All the Time

Expedia has some of the best wine hotels in the U.S. We have everything from luxury hotels with pools, spas, and award-winning bistros to accommodations that provide just enough to make sure you are relaxed on vacation. And no matter what hotel you choose, rest easy knowing that you'll be welcomed with a comfortable bed, plenty of amenities, and accommodations not far from The Berkshires's wineries.

Once you check out your room, begin your grape adventure at some of The Berkshires's best wineries. You'll find there isn't a more relaxing holiday than walking down rows of grape vines and exploring wine caves, all while enjoying the results of so much dedication and hard work. From fruit-forward Zinfandels to big tannin Sangioveses, even a trip to one winery can be an adventure unto itself. Tasting local wines while also being surrounded by the same vineyards and the people that produced them is a unique experience that not many getaways can offer.

Reserve Your Winery Hotel in The Berkshires Today!

Wine has been the inspiration for numerous songs, movies, books, and poems. And it could also inspire your next great vacation We have hotels near The Berkshires wineries for most budgets. If you're unsure what hotel to choose, then make sure to read thorough our review section to see which lodging is the best fit for your vacation. These deals won't last long. Book soon to get the hotel for your The Berkshires wine-infused getaway.

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