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Winery Hotels & Resorts in The Berkshires from NZ$218

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Check availability on The Berkshires Winery Hotels

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov

Our top choices for The Berkshires hotels with winery

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

1. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (935 reviews)
"Super clean and cozy and safe"
United States
Andrea
The price is NZ$119
includes taxes & fees
2 Nov - 3 Nov
Monument Mountain Motel
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
United States
Md
The price is NZ$319
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

3. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (851 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is NZ$165
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

4. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is NZ$140
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Great Barrington
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

5. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,003 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is NZ$218
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A calm lake at dusk with a wooden dock and two chairs facing the water.

6. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is NZ$216
includes taxes & fees
6 Nov - 7 Nov
Berkshire Lake Lodge
A red building with a sign reading "Shaker Mill Inn."

7. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is NZ$212
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
Interior detail

8. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is NZ$344
includes taxes & fees
2 Nov - 3 Nov
Wilder House Berkshires
Two Adirondack chairs facing a river with a forested hill in the background.

9. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"The location was good for our trip."
United States
Basil
The price is NZ$196
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

10. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay"
United States
Michael
The price is NZ$267
includes taxes & fees
5 Nov - 6 Nov
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

11. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is NZ$268
includes taxes & fees
17 Nov - 18 Nov
East Rock Inn
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

12. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 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"
United States
Francis
The price is NZ$268
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
Room

13. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!"
United States
Vandhana
The price is NZ$226
includes taxes & fees
29 Nov - 30 Nov
Courtyard by Marriott Lenox Berkshires
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

14. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for a travel stop-over."
United States
James
The price is NZ$163
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

15. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is NZ$235
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
Exterior

16. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,251 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is NZ$204
includes taxes & fees
8 Nov - 9 Nov
Berkshire Mountain Lodge
A building entrance with a large planter with purple flowers and a small tree.

17. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (972 reviews)
"Very nice hotel"
United States
Philip
The price is NZ$230
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
A spacious hotel lobby with multiple seating areas, large windows, and a television.

18. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is NZ$218
includes taxes & fees
7 Nov - 8 Nov
Hampton Inn & Suites Berkshires-Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

19. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,057 reviews)
"A very good place to stay"
United States
Madhavi R
The price is NZ$242
includes taxes & fees
29 Nov - 30 Nov
Berkshires Untold
An indoor swimming pool with clear water, tiled floors, and a blue wall.

20. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (253 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
United States
Yuguo
The price is NZ$204
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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.
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Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The Yankee Inn was clean and on a beautiful property. The beds were extremely comfortable. We enjoyed the morning breakfast, and the staff was extremely kind and helpful. If you book through Expedia - I would call ahead to verify the specifics of the room you have reserved, as Expedia’s description of the room I reserved didn’t match the description on the actual Yankee Inn website. Through Expedia, I reserved a King Deluxe with fireplace, balcony and mountain view. But the actual Yankee Inn website offers EITHER a King Deluxe with a fireplace and balcony OR King Deluxe with mountain view. The management made amends to accommodate as much as possible, but the Expedia advertising was a bit misleading in my opinion."
Kimberly 2-night trip
Posted 2 days ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I booked this for one of my bus drivers & he told me he had a good time theree in the hotel. Clean & quiet."
Smath 1-night trip
Posted 2 days ago
Quality Inn Great Barrington

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