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Romantic Hotels in The Berkshires, Massachusetts
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Our top choices for The Berkshires romantic hotels
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
Linda
The price is P5,443
P6,080 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very Good, (998)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
Frank
The price is P5,181
P5,788 total
includes taxes & fees
Jan 3 - Jan 4, 2026
9.0 out of 10, Wonderful, (821)
"Easiest check in and out. Great food in dining room. "
William
The price is P7,440
P8,311 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.8 out of 10, Excellent, (1001)
"Old time charm and hot tub under the stars"
Lori
The price is P8,753
P12,402 total
includes taxes & fees
Jan 26 - Jan 27, 2026
9.6 out of 10, Exceptional, (554)
"staff was great"
Tim
The price is P12,866
P14,371 total
includes taxes & fees
Jan 1 - Jan 2, 2026
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
Christopher
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."
Lynda
The price is P10,897
P11,954 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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 ChesterwoodStockbridge
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. "
Robert
The price is P22,437
P27,142 total
includes taxes & fees
Jan 13 - Jan 14, 2026
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.
Top The Berkshires Hotel Reviews
The Red Lion Inn
10/10 Excellent
Hampton Inn & Suites Berkshires-Lenox
10/10 Excellent