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Romantic Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Romantic Hotels

Tonight
Sep 30 - Oct 1
Tomorrow
Oct 1 - Oct 2
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for The Berkshires romantic hotels

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
William
P6,759
P7,550 total
includes taxes & fees
Oct 27 - Oct 28
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside dock with kayaks and a covered boat ramp.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
P8,458
P9,448 total
includes taxes & fees
Oct 29 - Oct 30
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

3. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
P10,053
P11,229 total
includes taxes & fees
Oct 26 - Oct 27
Berkshires Untold
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.

4. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
P9,604
P11,015 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
P11,118
P15,526 total
includes taxes & fees
Oct 19 - Oct 20
The Red Lion Inn
Interior detail
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.
A room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.
A bedroom with a large bed, a dresser, a chair, and a mirror.

6. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
P12,908
P14,418 total
includes taxes & fees
Oct 25 - Oct 26
Wilder House Berkshires
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden wall with a white pendant light fixture.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

7. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
P26,191
P31,352 total
includes taxes & fees
Oct 1 - Oct 2
Prospect Berkshires
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 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.

8. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
P8,942
P9,988 total
includes taxes & fees
Oct 19 - Oct 20
East Rock Inn
A red building with a sign reading "Shaker Mill Inn."
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

9. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
P11,195
P12,281 total
includes taxes & fees
Oct 1 - Oct 2
Shaker Mill Inn
Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.
A row of colorful Victorian-style houses with a prominent red one labeled "PORCHES."
Two people sitting by a campfire in a wooded area with benches and a clear view of the surrounding trees.
A cozy living room with a fireplace, a red armchair, a bookshelf, and a coffee table.

10. The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA
North Adams
United States
Ram
P12,414
P15,265 total
includes taxes & fees
Oct 29 - Oct 30
The Porches Inn at Mass MoCA
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Very nice room, great price"
Bill 2-night trip
Posted 5 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"One of the most unique establishments in the US. It brings one back to time when life was much simpler. Highly recomended."
Michael 1-night trip
Posted 2 days ago
The Red Lion Inn

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