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Find Romantic Hotels in The Berkshires, MA

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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, (1007)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is ₩141,664
₩158,239 total
includes taxes & fees
Jan 9 - Jan 10
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (832)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is ₩158,395
₩176,928 total
includes taxes & fees
Jan 11 - Jan 12
Berkshires Untold

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ₩146,120
₩163,216 total
includes taxes & fees
Jan 19 - Jan 20
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, (1005)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ₩216,689
₩306,586 total
includes taxes & fees
Jan 14 - Jan 15
The Red Lion Inn

The Williams Inn

The Williams Inn
4.0 star property
Williamstown
9.6 out of 10, Exceptional, (558)
"Great staff, great rooms, we had a little issue with the door not opening, but they were quick to fix it. Bar staff, fantastic! Restaurant (we had brunch) delicious. This is our go to hotel when we stay in the Berkshires "
United States
James
The price is ₩269,089
₩300,572 total
includes taxes & fees
Jan 11 - Jan 12
The Williams Inn

Brook Farm Inn

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

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (133)
"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 ₩267,957
₩293,949 total
includes taxes & fees
Jan 7 - Jan 8
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)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is ₩551,718
₩667,422 total
includes taxes & fees
Feb 5 - Feb 6
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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