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
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
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
Gustavo
AED 421
AED 471 total
includes taxes & fees
8 Nov - 9 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 cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
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 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 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
Robin
AED 893
AED 1,042 total
includes taxes & fees
3 Nov - 4 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 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 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 534
AED 597 total
includes taxes & fees
1 Nov - 2 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 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.
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 1,378 total
includes taxes & fees
27 Oct - 28 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 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 2,581 total
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

7. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,107
AED 2,281 total
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
View all properties

Top Lenox Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"
Kimberly 2-night trip
Posted 12 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Beds were comfortable, room was clean, train was not often"
Patricia 3-night trip
Posted 2 days ago
Quality Inn Great Barrington
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."
Alexandra 1-night trip
Posted 2 days ago
The Cornell Inn, Lenox & The Berkshires

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