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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

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 NT$4,294
NT$7,184 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 NT$4,151
NT$4,637 total
includes taxes & fees
Dec 12 - Dec 13
The Yankee Inn
A building entrance with a large planter with purple flowers and a small tree.

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 NT$3,817
NT$4,264 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

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 NT$3,457
NT$3,862 total
includes taxes & fees
Nov 18 - Nov 19
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 NT$3,501
NT$3,910 total
includes taxes & fees
Dec 13 - Dec 14
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A large building with a prominent tower, surrounded by trees and a winding road.

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 NT$2,523
NT$3,553 total
includes taxes & fees
Dec 10 - Dec 11
Berkshire Mountain Lodge
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

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 NT$1,968
NT$2,198 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 NT$5,590
NT$6,411 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 NT$2,641
NT$3,311 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 NT$3,633
NT$4,701 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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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."
Johanna 1-night trip
Posted 8 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved the place & desk staff . Breakfast room staff was curt and dismissive."
Stephen Bond 2-night trip
Posted 1 day ago
The Red Lion Inn

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