The Best Winery Hotels in Lenox, MA from AED 471 in 2026 | Expedia

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Check availability on Lenox Winery Hotels

Tonight

13 Oct - 14 Oct

Tomorrow

14 Oct - 15 Oct

This weekend

16 Oct - 18 Oct

Next weekend

23 Oct - 25 Oct

Our top choices for Lenox hotels with winery

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

A dining table set with a vase of flowers, a book, and cutlery.

1. Brook Farm Inn

Lenox

United States

Carrie

AED 714

AED 827 total

includes taxes & fees

2 Nov - 3 Nov

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A lakeside dock with kayaks and a covered boat ramp.

A dining area with large windows, wooden furniture, and a view of a lake.

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

Lee

United States

Gustavo

AED 421

AED 471 total

includes taxes & fees

8 Nov - 9 Nov

A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.

A grand piano in a living room with a sofa, a chandelier, and a fireplace.

A sign for Gateways Inn advertising mat and mimosa services, with a garden area in the background.

A grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.

3. Gateways Inn & Restaurant

Lenox

AED 893

AED 1,042 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

A hotel room with two beds, a desk, a TV, and a window with curtains.

4. East Rock Inn

Great Barrington

United States

ERIK

AED 508

AED 567 total

includes taxes & fees

13 Nov - 14 Nov

A two-story house with a balcony, a deck, and a view of the surrounding forest.

A modern kitchen with white cabinets and a built-in knife block.

A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.

A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

5. Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

AED 1,140

AED 2,322 total

includes taxes & fees

18 Oct - 19 Oct

A wooden cabin with a porch, a grill, and a flower planter.

A kitchen with wooden cabinets, a built-in oven, a sink, and a refrigerator.

A cozy living room with a grey sofa, a wooden coffee table, a fireplace, and a television mounted above it.

A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

6. Ideal location for summer and winter activities with plenty of outdoor space.

Hillsdale

United States

Richard M.

AED 771

AED 1,440 total

includes taxes & fees

14 Oct - 15 Oct

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

A cabin in a forest with a dirt path leading to it, surrounded by trees.

A cozy interior with a loft bed, a small kitchenette, and a welcoming 'Welcome' mat.

A triangular-shaped building with a balcony and a wooden picnic table in front.

7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

United States

Sharon K.

AED 536

AED 1,378 total

includes taxes & fees

14 Oct - 15 Oct

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

A dining room with a brick fireplace, white chairs, a wooden table, and a fruit basket.

A garden patio with Adirondack chairs, a stone wall, and a wooden fence.

A fireplace with a clock above it, wooden beams, and a sofa in a living room.

8. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

United States

Mark M.

AED 1,469

AED 2,581 total

includes taxes & fees

19 Oct - 20 Oct

View all properties

Top Lenox Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent

"Really enjoyed our one night stay in this hotel"

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