Romantic Hotels in The Berkshires, Massachusetts

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

This weekend
Next weekend

Top The Berkshires Romantic Hotels

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (417)
"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 P10,855
P11,908 total
includes taxes & fees
Jul 30 - Jul 31
Shaker Mill Inn

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1908)
"Great stay with all plenty of things to do…"
The price is P4,963
P6,170 total
includes taxes & fees
Aug 25 - Aug 26
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (837)
"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 P7,027
P7,849 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Dewey

3.5 star property
8.8 out of 10, Excellent, (316)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is P12,626
P14,103 total
includes taxes & fees
Aug 26 - Aug 27
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 P24,900
P30,122 total
includes taxes & fees
Aug 4 - Aug 5
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, (122)
"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, (1009)
"Iconic, comfortable, historic ambiance, convenient location. If you come to the Berkshires you should stay or eat here at least once. Basic room with grandma's attic furniture but with a renovated bathroom. Breakfast and lunch were very good."
The price is P11,369
P15,251 total
includes taxes & fees
Aug 25 - Aug 26
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 P11,761
P13,137 total
includes taxes & fees
Jul 31 - Aug 1
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