Romantic Hotels in The Berkshires, Massachusetts

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Top The Berkshires Romantic Hotels

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (419)
"Nice stay"
The price is P10,220
P11,211 total
includes taxes & fees
Aug 12 - Aug 13
Shaker Mill Inn

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1941)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is P6,184
P7,534 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (854)
"Consistently a clean room with welcoming staff."
The price is P6,566
P7,334 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P9,992
P11,161 total
includes taxes & fees
Sep 2 - Sep 3
The Dewey

Chestnut Lodge

3.5 star property
2.0 out of 10, (2)
"An absolutely horrible experience! My family (2 adults and my 6 year old son) had reserved this so-called hotel for $284 in June for a 13th Aug stay. After a full day at the Berkshires, we checked-in at 6 pm. This place is in a terrible location (unpaved roads, still-in construction steps). To our horror we found that the room had No Air-Conditioning. It was 90 degrees outside and all they had in the room was a ceiling fan. There were bugs in the room due to the heat. On top of it all the...
Chestnut Lodge

Kemble Inn

3.5 star property
8.8 out of 10, Excellent, (31)
"Memorable. A wonderful hotel I every aspect. Faultless service from Scoyt and the team"
Kemble Inn

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is P22,397
P27,094 total
includes taxes & fees
Aug 25 - Aug 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is P10,791
P14,605 total
includes taxes & fees
Aug 12 - Aug 13
The Red Lion Inn

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (638)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is P8,480
P9,472 total
includes taxes & fees
Sep 7 - Sep 8
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.

Top The Berkshires Hotel Reviews