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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
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 modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

1. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
AED 376
AED 420 total
includes taxes & fees
8 Nov - 9 Nov
The Yankee Inn
A lodge with a large building and a dock by a lake, surrounded by forest.
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.
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
AED 400
AED 446 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 modern living room with a fireplace, comfortable seating, and a large window with curtains.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
A dining area with a glass table, red walls, and framed artwork.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
AED 564
AED 647 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.
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 cozy library with bookshelves, a fireplace, and comfortable seating.

4. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 478
AED 534 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 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
Mallory
AED 579
AED 829 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Dining
Interior
Interior
Living area

6. Garden Gables

Garden Gables
Lenox
AED 480
AED 803 total
includes taxes & fees
26 Oct - 27 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
AED 426
AED 467 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 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 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
AED 490
AED 547 total
includes taxes & fees
25 Nov - 26 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.
Room
A wooden wall with a white pendant light fixture.

9. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
AED 916
AED 1,147 total
includes taxes & fees
9 Nov - 10 Nov
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
AED 637
AED 712 total
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
View all properties

Top The Berkshires Hotel Reviews

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 3 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 6 hours ago
The Cornell Inn, Lenox & The Berkshires

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