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
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
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 dining area with large windows, wooden furniture, and a view of a lake.
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
Gustavo
AED 400
AED 446 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A room with a large ornate mirror above a white fireplace, floral wallpaper, and a chair visible in the reflection.
A dining table set with a vase of flowers, a book, and cutlery.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

2. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
AED 714
AED 827 total
includes taxes & fees
26 Oct - 27 Oct
Brook Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.
A grand staircase with a wooden handrail and patterned carpet, leading to an upper floor.
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
Robin
AED 847
AED 989 total
includes taxes & fees
25 Oct - 26 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 hotel room with two beds, a desk, a TV, and a window with curtains.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

4. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
AED 460
AED 513 total
includes taxes & fees
24 Nov - 25 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 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.
A triangular-shaped building with a balcony and a wooden picnic table in front.

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 1,382 total
includes taxes & fees
26 Oct - 27 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A wooden cabin with a porch, a grill, and a flower planter.
A kitchen with wooden cabinets, a built-in oven, a sink, and a refrigerator.
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.

6. 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
Richard M.
AED 771
AED 1,485 total
includes taxes & fees
25 Oct - 26 Oct
Ideal location for summer and winter activities with plenty of outdoor space.
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 garden patio with Adirondack chairs, a stone wall, and a wooden fence.

7. 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
16 Nov - 17 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
View all properties

Top Lenox Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
Sandra 1-night trip
Posted 4 hours ago
The Cornell Inn, Lenox & The Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I would prefer more flexibility making reservations. Online and by phone, I wanted two rooms for two people. I was forced to request two rooms for THREE people to work around the algorithm that allowed only one room for two people. Also I was forced to accept two rooms in the same price range, when I wanted one premium king, not two. I left another hotel due to their inflexibility, and I will choose one with a personal approach next time."
Joan 2-night trip
Posted 6 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Clean large room. Nice bathroom Walling distance to downtown and many restaurant options."
Denise 1-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"We enjoyed our stay, staff was very friendly."
Michael 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox

Explore a world of travel with Expedia