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Check availability on The Berkshires Romantic Hotels

Our top choices for The Berkshires romantic hotels

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is ₩233,220
₩260,504 total
includes taxes & fees
Jul 22 - Jul 23
The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,007 reviews)
"The staff were super friendly"
United States
John
The price is ₩324,521
₩373,364 total
includes taxes & fees
Jul 20 - Jul 21
The Cornell Inn, Lenox & The Berkshires

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,040 reviews)
"Great location too"
United States
judith
The price is ₩199,774
₩256,546 total
includes taxes & fees
Aug 13 - Aug 14
Berkshire Mountain Lodge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,016 reviews)
"Nice place to stay."
United States
Debra
The price is ₩287,376
₩320,995 total
includes taxes & fees
Jul 29 - Jul 30
Berkshires Untold

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,014 reviews)
"Excellent stay. Such history and attention to detail. Some areas showing some wear but this is a great place to stay."
United States
Allen
The price is ₩254,748
₩351,350 total
includes taxes & fees
Jul 22 - Jul 23
The Red Lion Inn

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (634 reviews)
"We arrived at the hotel and there was"
United States
Nancy
The price is ₩291,002
₩325,049 total
includes taxes & fees
Jul 19 - Jul 20
Courtyard by Marriott Lenox Berkshires

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, (1,013 reviews)
"enjoyable stay"
United States
James
The price is ₩319,556
₩356,946 total
includes taxes & fees
Jul 20 - Jul 21
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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, (133 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is ₩272,075
₩303,907 total
includes taxes & fees
Aug 9 - Aug 10
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (873 reviews)
"Love the hotel even the creaky floors, great stay, good food. The only thing missing from this hotel is breakfast"
United States
Jim
The price is ₩372,255
₩415,808 total
includes taxes & fees
Jul 30 - Jul 31
Hotel On North

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, (789 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ₩207,895
₩232,218 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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.

Find out more about The Berkshires

The Berkshires attractions for couples

The Berkshires beckon with a blend of culture, nature, and adventure, perfect for the discerning traveler seeking quality experiences. Start your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class music amid breathtaking natural scenery. For art enthusiasts, the Norman Rockwell Museum in Stockbridge offers an intimate look at the beloved artist's life and works, set against the charming backdrop of New England. Families can explore the interactive exhibits at the Berkshire Museum in Pittsfield, which combines art, history, and science to engage visitors of all ages. Outdoor lovers will relish a hike in the scenic Mount Greylock State Reservation, where the highest peak in Massachusetts provides stunning panoramic views and serene trails. After a day of exploration, consider staying in Lenox, where luxury hotels like the 19th-century Blantyre estate offer a unique blend of historic charm and modern comforts, ensuring attentive service and a pampered experience. The blend of activities and high-end accommodations in The Berkshires creates an enjoyable getaway that caters to your every need.

Top The Berkshires Hotel Reviews