Find Romantic Hotels in The Berkshires from S$148

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Top Romantic Hotels in The Berkshires

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (416)
"Very cute and clean room. After driving all day we were so happy to see all muffins, scones, yogurt, cereal, oatmeal, strawberries, milk, OJ, hot chocolate and coffee already in the room for breakfast the next day. We had a great stay, thank you!"
The price is S$241
includes taxes & fees
30 Jul - 31 Jul
Shaker Mill Inn

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1895)
"Great stay with all plenty of things to do…"
The price is S$148
includes taxes & fees
18 Aug - 19 Aug
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (829)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "
The price is S$184
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Dewey

3.5 star property
8.8 out of 10, Excellent, (315)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is S$308
includes taxes & fees
13 Aug - 14 Aug
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 S$666
includes taxes & fees
4 Aug - 5 Aug
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, (121)
"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, (1004)
"I had excellent stay at the Red Lion Inn "
The price is S$328
includes taxes & fees
13 Aug - 14 Aug
The Red Lion Inn

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"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 S$277
includes taxes & fees
27 Jul - 28 Jul
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