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Most Romantic Hotels in The Berkshires

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Check availability on The Berkshires Romantic Hotels

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

Our top choices for The Berkshires romantic hotels

Two Adirondack chairs facing a river with a forested hill in the background.
A restaurant interior with white tables, cushioned booths, and a bar area.
A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
RM433
RM484 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A lakeside dock with kayaks and a covered boat ramp.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
RM445
RM497 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.
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.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
RM627
RM719 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
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
RM532
RM594 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A straw hat, sunglasses, and two drinks on a striped towel by a body of water.
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.
A covered porch with wicker furniture and hanging flower baskets.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
RM644
RM922 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Dining
Living area
Room
Interior

6. Garden Gables

Garden Gables
Lenox
RM534
RM893 total
includes taxes & fees
27 Oct - 28 Oct
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 stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

7. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mahadeva
RM466
RM511 total
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.
A grassy outdoor area with four blue Adirondack chairs arranged in a circle.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.

8. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
RM552
RM617 total
includes taxes & fees
17 Nov - 18 Nov
East Rock Inn
A wooden boat on calm water with a house in the background.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden wall with a white pendant light fixture.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.

9. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
RM1,158
RM1,431 total
includes taxes & fees
9 Nov - 10 Nov
Prospect Berkshires
Interior detail
A cozy living room with a fireplace, a bookshelf, a coffee table with a book, and a plaid sofa.
A sign for 'Wilder House' with a maple leaf logo, established in 2023, and a date of 2023.
A bedroom with a large bed, a dresser, a chair, and a mirror.

10. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Liliana
RM669
RM748 total
includes taxes & fees
1 Nov - 2 Nov
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 12 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 14 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 17 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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