Romantic Hotels in The Berkshires, Massachusetts

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Check prices for these dates

Tonight
Nov 14 - Nov 15
Tomorrow
Nov 15 - Nov 16
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for The Berkshires romantic hotels

A modern bedroom with a four-poster bed, a fireplace, and a large floral mural on the wall.

1. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
The price is P8,324
P13,925 total
includes taxes & fees
Nov 15 - Nov 16
Garden Gables
Two Adirondack chairs facing a river with a forested hill in the background.

2. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,004 reviews)
"The location was good for our trip."
United States
Basil
The price is P8,029
P8,969 total
includes taxes & fees
Dec 12 - Dec 13
The Yankee Inn
A multi-story hotel with a classic facade, large windows, and a prominent entrance.

3. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (985 reviews)
"Staff very pleasant and accommodating."
United States
Rosemarie
The price is P7,399
P8,264 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
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
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,073 reviews)
"Nice Hotel"
United States
Juan
The price is P6,697
P7,480 total
includes taxes & fees
Dec 14 - Dec 15
Berkshires Untold
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,002 reviews)
"clean room - pleasant staff"
United States
Tina
The price is P6,771
P7,563 total
includes taxes & fees
Dec 13 - Dec 14
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,273 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is P4,888
P6,883 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A neatly made bed with white linens, two bedside lamps, a nightstand with a telephone, and a painting on the wall.

7. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (944 reviews)
"Clean, reasonably priced, convenient"
United States
Martha
The price is P3,814
P4,260 total
includes taxes & fees
Nov 15 - Nov 16
Monument Mountain Motel
A snow-covered outdoor area with a patio, seating, and a covered dining area.

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is P10,834
P12,427 total
includes taxes & fees
Nov 15 - Nov 16
The Cornell Inn, Lenox & The Berkshires
Indoor pool

9. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,851 reviews)
"Gorgeous setting, comfortable beds and luxurious accommodations."
United States
Carol
The price is P5,117
P6,414 total
includes taxes & fees
Nov 15 - Nov 16
Vacation Village in the Berkshires
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

10. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
3.5 star property
South Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay"
United States
Michael
The price is P7,037
P9,105 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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