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
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 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.
A dining area with large windows, wooden furniture, and a view of a lake.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AED 425
AED 474 total
includes taxes & fees
1 Nov - 2 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 cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A dining table set with a vase of flowers, a book, and cutlery.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

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 two-story building with a covered entrance and a large 'G' sign.
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.

3. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Erin
AED 949
AED 1,107 total
includes taxes & fees
5 Nov - 6 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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.

4. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AED 478
AED 534 total
includes taxes & fees
4 Nov - 5 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 536
AED 1,378 total
includes taxes & fees
7 Oct - 8 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 garden patio with Adirondack chairs, a stone wall, and a wooden fence.
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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mark M.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden cabin with a porch, a grill, and a flower planter.
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.
A kitchen with wooden cabinets, a built-in oven, a sink, and a refrigerator.

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 735
AED 1,403 total
includes taxes & fees
6 Oct - 7 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 kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A modern kitchen with white cabinets and a built-in knife block.

8. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,207
AED 2,404 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
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Top Lenox Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted less than an hour ago
Quality Inn Great Barrington

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