A person snowboarding down a snowy slope.

Winery Hotels & Resorts in The Berkshires from AU$196

  • 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 The Berkshires Winery Hotels

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for The Berkshires 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
James
AU$199
includes taxes & fees
14 Sept - 15 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
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.
A hotel room with two beds, a desk, a TV, and a window with curtains.

2. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AU$196
includes taxes & fees
7 Sept - 8 Sept
East Rock Inn
A greenhouse with a transparent roof, a seating area with cushions, and a potted plant.
A living room with a grey sectional sofa, a small round coffee table, a brown leather armchair, and a window with curtains.
A cozy library with wooden bookshelves, a reading area, and a fireplace.
A living room with a fireplace, sofa, armchair, and a TV.

3. Berkshire Valley Inn

Berkshire Valley Inn
Williamstown
United States
DM
AU$259
includes taxes & fees
7 Sept - 8 Sept
Berkshire Valley Inn
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 loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.
A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

4. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
AU$442
includes taxes & fees
30 Aug - 31 Aug
Brook Farm 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 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.
AU$542
includes taxes & fees
9 Sept - 10 Sept
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 cozy living room with a fireplace, a clock, and a bookshelf.
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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mary R.
AU$772
includes taxes & fees
1 Sept - 2 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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 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.

7. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Louise
AU$372
includes taxes & fees
17 Sept - 18 Sept
Gateways Inn & Restaurant
A residential garden with a pathway leading to a house.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and flowers.
A circular outdoor fire pit with a metal rim, surrounded by gravel.
A residential property with a swimming pool, a covered patio area, and a well-maintained lawn.

8. The Amelia

The Amelia
Hudson
United States
Kylene
AU$576
includes taxes & fees
30 Aug - 31 Aug
The Amelia
A room with a large sliding glass door leading to a balcony with cherry blossom trees.
A bar area with a dark wood bar counter, multiple shelves of liquor bottles, and hanging wine glasses.
A modern living room with a sofa, coffee table, TV, wooden shelves, and a staircase.
A building with a white brick exterior, a wooden door, and a bench outside.

9. Wm. Farmer & Sons

Wm. Farmer & Sons
Hudson
United States
Lori
AU$314
includes taxes & fees
30 Aug - 31 Aug
Wm. Farmer & Sons
A bedroom with a bed, bedside table, and a wall-mounted mirror.
A staircase with white steps and black non-slip treads, leading to a landing with a dark wall and a window with colorful stained glass.
A room with a desk, chair, and a brown leather chair. There is a white door leading to a bathroom with a sink and a mirror.
A building with a sign reading "NAUTICAL NEST" and a lantern above it.

10. Nautical Nest

Nautical Nest
Hudson
United States
Jill D
AU$250
includes taxes & fees
31 Aug - 1 Sept
Nautical Nest
View all properties

Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 7 hours ago
The Yankee Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox

Explore a world of travel with Expedia