Find Romantic Hotels in The Berkshires, MA

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on The Berkshires Romantic Hotels

Compare The Berkshires Romantic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (410)
"Nice"
The price is AED 702
AED 770 total
includes taxes & fees
3 Jun - 4 Jun
Shaker Mill Inn

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1804)
"The property was clean and the staff very accommodated."
The price is AED 434
AED 525 total
includes taxes & fees
18 May - 19 May
Vacation Village in the Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (782)
"Great place."
The price is AED 400
AED 447 total
includes taxes & fees
18 May - 19 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Dewey

3.5 star property
8.8 out of 10, Excellent, (311)
"We would definitely stay here again! "
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)
"wonderfully restored old mansion. Rooms were charming... nicely designed. In fact the entire facility has been thoughtfully brought into today's design standards. Very accomodating staff... although many appeared to be a training mode. Need to improve the professionalism a bit. They have a new general manager (had only been there about 2 weeks when we visited)... seems he has a number of things on his agenda that will improve the property even more. Food was good... but not wonderful. ...
Kemble Inn

Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

10.0 out of 10, Exceptional, (94)
"Great location and beautifully appointed house. Cindy is very helpful and responsive."
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow

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 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)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"Quaint & hospitable!"
The price is AED 531
AED 757 total
includes taxes & fees
28 May - 29 May
The Red Lion Inn
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.
Don't see what you're looking for?
See all available properties in The Berkshires