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

Find Winery Hotels in Lenox, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Lenox Winery Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

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
Gustavo
AED 418
AED 467 total
includes taxes & fees
15 Nov - 16 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 bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.
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 two-story building with a covered entrance and a large 'G' sign.
A sign for Gateways Inn advertising mat and mimosa services, with a garden area in the background.
A grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.

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
Sharon
AED 442
AED 493 total
includes taxes & fees
17 Nov - 18 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 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.
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
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 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 2,581 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 spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.
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.

7. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
AED 1,008
AED 2,154 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

8/10 Good
"The hotel is in a good location. There are some good restaurants within walking distance. Only one complaint is that the bathroom fan is very loud."
Cynthia 3-night trip
Posted 15 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room and the hotel looked very clean, and the staff were very friendly. Also, the breakfast offered a good variety."
Luisa 1-night trip
Posted 20 hours ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Clean, parking, room all good. Staff was very welcome and helpful."
Avi 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Our room was very nice with a comfortable bed, but the door to the room did not fit properly so lots of light came through the edges. Also we could hear the guests above us ( we were on first floor in carriage house) tramping around at 6:00 am. It would help to carpet the floors. The breakfast, which was much hyped, was only okay. The ingredients were nothing special, for example the bread used for toast appeared to be off the grocery store shelf."
Benjamin 2-night trip
Posted 3 days ago
The Cornell Inn, Lenox & The Berkshires

Explore a world of travel with Expedia