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
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 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 dock with kayaks and a covered boat ramp.
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
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 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
2 Nov - 3 Nov
Brook Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.
A sign for Gateways Inn advertising mat and mimosa services, with a garden area in the background.
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.

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 grassy outdoor area with four blue Adirondack chairs arranged in a circle.
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
ERIK
AED 535
AED 598 total
includes taxes & fees
7 Nov - 8 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 interior with a loft bed, a small kitchenette, and a welcoming 'Welcome' mat.
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 585
AED 1,437 total
includes taxes & fees
8 Oct - 9 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 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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mark M.
AED 1,491
AED 2,577 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 735
AED 1,395 total
includes taxes & fees
8 Oct - 9 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 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 1,256
AED 2,468 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
View all properties

Top Lenox Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"
F. Cole 1-night trip
Posted 18 hours ago
The Cornell Inn, Lenox & The Berkshires
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 2 days ago
Quality Inn Great Barrington

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