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Winery Hotels & Resorts in The Berkshires from AU$188

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Check availability on The Berkshires Winery Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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 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.

1. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AU$188
includes taxes & fees
10 Nov - 11 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 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 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.

2. Brook Farm Inn

Brook Farm Inn
Lenox
United States
Carrie
AU$324
includes taxes & fees
2 Nov - 3 Nov
Brook Farm Inn
A Yale keypad lock on a yellow door.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
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.

3. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AU$204
includes taxes & fees
10 Nov - 11 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 cabin in a forest with a dirt path leading to it, surrounded by trees.
A triangular-shaped building with a balcony and a wooden picnic table in front.

4. 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
14 Oct - 15 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.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
United States
Mark M.
AU$981
includes taxes & fees
19 Oct - 20 Oct
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 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.
A grand piano in a living room with a sofa, a chandelier, and a fireplace.

6. Gateways Inn & Restaurant

Gateways Inn & Restaurant
Lenox
United States
Robin
AU$386
includes taxes & fees
3 Nov - 4 Nov
Gateways Inn & Restaurant
A residential garden with a pathway leading to a house.
A circular outdoor fire pit with a metal rim, surrounded by gravel.
A modern kitchen with white cabinetry, a built-in oven, and a coffee machine. There are shelves with glassware and a window providing natural light.
A residential property with a swimming pool, a covered patio area, and a well-maintained lawn.

7. The Amelia

The Amelia
Hudson
United States
Divya
AU$386
includes taxes & fees
9 Nov - 10 Nov
The Amelia
A bedroom with a bed, bedside table, and a wall-mounted mirror.
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.
An outdoor patio with a wooden table and four black wire chairs, surrounded by stone tiles and greenery.
A building with a sign reading "NAUTICAL NEST" and a lantern above it.

8. Nautical Nest

Nautical Nest
Hudson
United States
Christina
AU$209
includes taxes & fees
10 Nov - 11 Nov
Nautical Nest
A room with a large sliding glass door leading to a balcony with cherry blossom trees.
A modern living room with a sofa, coffee table, TV, wooden shelves, and a staircase.
A long dining table with chairs, a chandelier, and a brick wall in the background.
A bar area with a dark wood bar counter, multiple shelves of liquor bottles, and hanging wine glasses.

9. Wm. Farmer & Sons

Wm. Farmer & Sons
Hudson
United States
Lori
AU$341
includes taxes & fees
9 Nov - 10 Nov
Wm. Farmer & Sons
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.
A fire pit with two Adirondack chairs, a table with drinks, and a house in the background.
A two-story house with a porch, a front door, and a mailbox.
A room with a white door, a window, and a wall with various framed pictures.

10. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
Craryville
United States
Thomas
AU$321
includes taxes & fees
19 Oct - 20 Oct
Changing Times Boutique Country Lodging
View all properties

Top The Berkshires Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"It was fine. No breakfast that I saw"
Michael 1-night trip
Posted 1 hour ago
Best Western Plus Berkshire Hills Inn & Suites
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Although it's an older hotel, it's well maintained.Clean and updated also very friendly staff."
Marti 1-night trip
Posted 6 hours ago
The Yankee Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

8/10 Good
"Nice Inn/B&B in Lenox MA, about a mile from downtown."
Anne 1-night trip
Posted 2 days 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 4 days ago
Quality Inn Great Barrington

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