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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22

Our top choices for The Berkshires romantic hotels

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

1. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (855 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
United States
Cynthia
The price is NT$2,727
NT$3,046 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Hotel & Suites Great Barrington by IHG
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

2. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (821 reviews)
"Nice view and location for fall color."
United States
Md
The price is NT$5,278
NT$5,895 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

3. Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (942 reviews)
"Clean, reasonably priced, convenient"
United States
Martha
The price is NT$1,966
NT$2,196 total
includes taxes & fees
Nov 9 - Nov 10
Monument Mountain Motel
A calm lake at dusk with a wooden dock and two chairs facing the water.

4. Berkshire Lake Lodge

Berkshire Lake Lodge
Lee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
United States
mike
The price is NT$3,584
NT$4,003 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Lake Lodge
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

5. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,003 reviews)
"Just perfect lodging place for short time travelers"
United States
Bernardo Jr
The price is NT$2,787
NT$3,113 total
includes taxes & fees
Dec 2 - Dec 3
Quality Inn Lee - Lenox South
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

6. 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, (1,001 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is NT$3,518
NT$3,930 total
includes taxes & fees
Dec 3 - Dec 4
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior detail

7. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
United States
Liliana
The price is NT$5,700
NT$6,367 total
includes taxes & fees
Nov 11 - Nov 12
Wilder House Berkshires
A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

8. East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
United States
Sharon
The price is NT$3,995
NT$4,462 total
includes taxes & fees
Dec 9 - Dec 10
East Rock Inn
A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

9. 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, (1,005 reviews)
"Nice place to stay"
United States
Michael
The price is NT$3,844
NT$4,936 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.

10. The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (96 reviews)
"Lovely property.unique historic buildings and rooms with updated amenities! Quiet and peaceful beautiful dinner!"
United States
mary ellen
The price is NT$9,527
NT$11,496 total
includes taxes & fees
Nov 9 - Nov 10
The Old Inn On The Green
An indoor swimming pool with clear water, tiled floors, and a blue wall.

11. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (258 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is NT$3,384
NT$3,780 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

12. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is NT$4,435
NT$4,954 total
includes taxes & fees
Nov 15 - Nov 16
Element by Marriott Lenox Berkshires
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

13. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (689 reviews)
"Great stay!"
United States
Vandhana
The price is NT$4,127
NT$4,609 total
includes taxes & fees
Nov 15 - Nov 16
Courtyard by Marriott Lenox Berkshires
Two Adirondack chairs facing a river with a forested hill in the background.

14. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The location was good for our trip."
United States
Basil
The price is NT$4,172
NT$4,660 total
includes taxes & fees
Nov 20 - Nov 21
The Yankee Inn
A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

15. Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Downtown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
United States
Lynne
The price is NT$2,485
NT$2,776 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Great Barrington
Exterior

16. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,262 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is NT$2,522
NT$3,550 total
includes taxes & fees
Dec 6 - Dec 7
Berkshire Mountain Lodge
A building entrance with a large planter with purple flowers and a small tree.

17. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (981 reviews)
"Very nice hotel"
United States
Philip
The price is NT$3,814
NT$4,260 total
includes taxes & fees
Nov 29 - Nov 30
Hotel On North
A spacious hotel lobby with multiple seating areas, large windows, and a television.

18. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,003 reviews)
"Breakfast was great"
United States
Thomas
The price is NT$3,602
NT$4,024 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn & Suites Berkshires-Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

19. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,067 reviews)
"Very nice place beautiful view"
United States
Brian
The price is NT$3,455
NT$3,859 total
includes taxes & fees
Nov 17 - Nov 18
Berkshires Untold
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

20. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is NT$3,899
NT$4,355 total
includes taxes & fees
Nov 15 - Nov 16
Hilton Garden Inn Lenox Pittsfield
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.
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stayed in an adjacent house owned by the hotel. When we booked we assumed we’d be in the main hotel. The “out” building was unmarked and hard to find. It was dark when we arrived and there were no porch lights. We thought the overall experience was good. Quaint but this building could benefit from some upgrades."
Randall 1-night trip
Posted 1 day ago
The Red Lion Inn

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