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

Find Winery Hotels in Lenox, MA

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Check availability on Lenox Winery Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

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 lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AED 431
AED 481 total
includes taxes & fees
10 Nov - 11 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 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.

2. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
AED 714
AED 827 total
includes taxes & fees
2 Nov - 3 Nov
Brook Farm Inn
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 grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.
A two-story building with a covered entrance and a large 'G' sign.

3. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Robin
AED 912
AED 1,065 total
includes taxes & fees
2 Nov - 3 Nov
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 sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

4. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AED 469
AED 523 total
includes taxes & fees
10 Nov - 11 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 triangular-shaped building with a balcony and a wooden picnic table in front.
A cozy living room with a grey sofa, a patterned throw blanket, and a wooden ceiling.
A cozy interior with a loft bed, a small kitchenette, and a welcoming 'Welcome' mat.

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 552
AED 1,396 total
includes taxes & fees
14 Oct - 15 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mark M.
AED 1,469
AED 2,552 total
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden cabin with a porch, a grill, and a flower planter.
A red cabin with a screened porch, a small deck, and a barbecue grill in a wooded area.
A kitchen with wooden cabinets, a built-in oven, a sink, and a refrigerator.
A cozy living room with a sofa, armchair, wooden coffee table, and a dining area with a table and chairs.

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

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
United States
Kenny
AED 771
AED 1,440 total
includes taxes & fees
12 Oct - 13 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A modern kitchen with white cabinets and a built-in knife block.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

8. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,157
AED 2,345 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
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Top Lenox Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Lovely room, comfortable bed and a nice breakfast."
judith 1-night trip
Posted 8 hours ago
The Cornell Inn, Lenox & The Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 1 day ago
The Yankee Inn

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