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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,000 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ¥15,760
¥17,603 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is ¥14,315
¥15,990 total
includes taxes & fees
Feb 22 - Feb 23
The Yankee, Trademark Collection by Wyndham

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is ¥22,102
¥31,591 total
includes taxes & fees
Mar 4 - Mar 5
The Red Lion Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (573 reviews)
"Very pleasant and relaxing place to stay"
United States
steve
The price is ¥29,211
¥32,629 total
includes taxes & fees
Mar 11 - Mar 12
The Williams Inn

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is ¥28,661
¥31,441 total
includes taxes & fees
Feb 16 - Feb 17
Gedney Farm

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ¥47,816
¥57,845 total
includes taxes & fees
Feb 24 - Feb 25
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (273 reviews)
"It was a cute property- just what we needed. Nice location!"
United States
Linda M.
The price is ¥20,859
¥32,447 total
includes taxes & fees
Feb 12 - Feb 13
Berkshire Village Carriage House - Super Private!!

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is ¥25,494
¥48,153 total
includes taxes & fees
Feb 12 - Feb 13
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

1896 House Country Inn & Motels

1896 House Country Inn & Motels
2.5 star property
Williamstown
6.6 out of 10, (448 reviews)
"Place was convenient, cleaned and quiet a little old, but all in all a good stay"
United States
Kelley
1896 House Country Inn & Motels
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

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