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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for The Berkshires romantic hotels

Two Adirondack chairs facing a river with a forested hill in the background.
A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A restaurant interior with white tables, cushioned booths, and a bar area.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
NT$3,456
NT$3,860 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
A lodge with a large building and a dock by a lake, surrounded by forest.
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 setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
NT$3,547
NT$3,962 total
includes taxes & fees
Nov 22 - Nov 23
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 modern living room with a fireplace, comfortable seating, and a large window with curtains.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
NT$5,003
NT$5,738 total
includes taxes & fees
Oct 27 - Oct 28
The Cornell Inn, Lenox & The Berkshires
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 sofa, a coffee table, and a large window with a view of trees.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

4. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
NT$4,244
NT$4,741 total
includes taxes & fees
Nov 1 - Nov 2
Berkshires Untold
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
NT$5,135
NT$7,356 total
includes taxes & fees
Nov 4 - Nov 5
The Red Lion Inn
Dining
Living area
Interior
Room

6. Garden Gables

Garden Gables
Lenox
NT$4,258
NT$7,124 total
includes taxes & fees
Oct 27 - Oct 28
Garden Gables
A red building with a sign reading "Shaker Mill Inn."
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
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.

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mahadeva
NT$3,782
NT$4,149 total
includes taxes & fees
Nov 2 - Nov 3
Shaker Mill Inn
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 hotel room with two beds, a desk, a TV, and a window with curtains.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.

8. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
NT$4,405
NT$4,920 total
includes taxes & fees
Nov 17 - Nov 18
East Rock Inn
A wooden boat on calm water with a house in the background.
Room
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.

9. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
NT$9,242
NT$11,416 total
includes taxes & fees
Nov 10 - Nov 11
Prospect Berkshires
Interior detail
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.
A sign for 'Wilder House' with a maple leaf logo, established in 2023, and a date of 2023.

10. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Liliana
NT$5,656
NT$6,318 total
includes taxes & fees
Oct 27 - Oct 28
Wilder House Berkshires
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"
Angelina 7-night trip
Posted 11 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Rooms were clean, nice beds and new kitchen accessories."
Linda 1-night trip
Posted 13 hours ago
Jiminy Peak Mountain Resort
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"We enjoyed a delicious home cooked breakfast! The staff was wonderful and very accommodating. Lots of ideas were given to us as to where to visit in the area."
Joan 1-night trip
Posted 16 hours ago
The Cornell Inn, Lenox & The Berkshires
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"The parking lot was being resurfaced and we could not find a handicap spot near the door. It was inconvenient, and one handicap spot was filled by a car without a handicap placard."
Marcia 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

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