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
29 Sep - 30 Sep
Tomorrow
30 Sep - 1 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 dock with kayaks and a covered boat ramp.
A lodge with a large building and a dock by a lake, surrounded by forest.
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 496
AED 555 total
includes taxes & fees
29 Oct - 30 Oct
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 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.
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 812
AED 937 total
includes taxes & fees
18 Oct - 19 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 grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.
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
Louise
AED 1,016
AED 1,185 total
includes taxes & fees
19 Oct - 20 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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.
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

East Rock Inn
Great Barrington
United States
ERIK
AED 492
AED 550 total
includes taxes & fees
30 Oct - 31 Oct
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 cabin in a forest with a dirt path leading to it, surrounded by trees.

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 1,296 total
includes taxes & fees
30 Sep - 1 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 modern kitchen with granite countertops, stainless steel appliances, and a blue island.
A fireplace with a clock above it, wooden beams, and a sofa in a living room.
A dining room with a brick fireplace, white chairs, a wooden table, and a fruit basket.

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 2,445 total
includes taxes & fees
30 Sep - 1 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 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.

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 1,316 total
includes taxes & fees
30 Sep - 1 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 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.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.

8. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,469
AED 2,583 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
View all properties

Top Lenox Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 16 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice room. Exceptionally clean. Great staff"
Daniel 3-night trip
Posted 22 hours ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 10 days ago
Howard Johnson by Wyndham Lenox

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