A town hall with a central dome and columns, surrounded by trees and people.

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Check availability on Lenox Winery Hotels

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Lenox hotels with winery

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
AED 412
AED 460 total
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
A dining table set with a vase of flowers, a book, and cutlery.
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.

2. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
AED 714
AED 827 total
includes taxes & fees
27 Oct - 28 Oct
Brook Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.
A two-story building with a covered entrance and a large 'G' sign.
A sign for Gateways Inn advertising mat and mimosa services, with a garden area in the background.
A grand piano in a living room with a sofa, a chandelier, and a fireplace.

3. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Robin
AED 891
AED 1,040 total
includes taxes & fees
26 Oct - 27 Oct
Gateways Inn & Restaurant
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

4. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
AED 445
AED 497 total
includes taxes & fees
19 Nov - 20 Nov
East Rock Inn
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 cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
United States
Sharon K.
AED 536
AED 1,382 total
includes taxes & fees
26 Oct - 27 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A bed with white bedding and two pillows, one plain white and one multicolored, against a teal wall with a wooden headboard.
A modern living room with a grey sofa set, a wooden coffee table, and a dining area with a table and chairs.
A modern kitchen with white cabinets, stainless steel appliances, and a large sliding glass door leading to a backyard.

6. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
Great Barrington
AED 1,743
AED 2,210 total
includes taxes & fees
23 Oct - 24 Oct
Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.
A fireplace with a clock above it, wooden beams, and a sofa in a living room.
A modern kitchen with granite countertops, stainless steel appliances, and a blue island.
A dining room with a brick fireplace, white chairs, a wooden table, and a fruit basket.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mark M.
AED 1,469
AED 2,581 total
includes taxes & fees
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
View all properties

Top Lenox Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place to stay, super friendly staff. All that the Lenox and Lee had to offer isn't far. Will stay again."
Jason 1-night trip
Posted 22 hours ago
The Cornell Inn, Lenox & The Berkshires
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"We enjoyed our stay, staff was very friendly."
Michael 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 2 days ago
Quality Inn Great Barrington

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