A person snowboarding down a snowy slope.

Find Romantic Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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 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
AED 389
AED 435 total
includes taxes & fees
1 Nov - 2 Nov
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
AED 425
AED 474 total
includes taxes & fees
1 Nov - 2 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 two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
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 States
Rosann
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.
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.
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".

4. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 484
AED 540 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 582
AED 832 total
includes taxes & fees
1 Nov - 2 Nov
The Red Lion Inn
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.

6. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 514
AED 564 total
includes taxes & fees
1 Nov - 2 Nov
Shaker Mill Inn
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 room with a wooden floor, two red armchairs, a small table, and a window with a view of trees.

7. Wilder House Berkshires

Wilder House Berkshires
Sheffield
United States
Mark
AED 758
AED 847 total
includes taxes & fees
25 Oct - 26 Oct
Wilder House Berkshires
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.
A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

8. Granville House

Granville House
Housatonic
United States
Nicole
AED 823
AED 919 total
includes taxes & fees
12 Oct - 13 Oct
Granville House
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.

9. East Rock Inn

East Rock Inn
Great Barrington
United States
ERIK
AED 482
AED 539 total
includes taxes & fees
1 Nov - 2 Nov
East Rock Inn
A two-story building with a sign reading "Chambéry Inn".
A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.
A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.
A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

10. Chambery Inn

Chambery Inn
Lee
United States
Alexandra
AED 922
AED 1,030 total
includes taxes & fees
2 Nov - 3 Nov
Chambery Inn
View all properties

Top The Berkshires Hotel Reviews

Explore a world of travel with Expedia