TOP Most Romantic Hotels in The Berkshires for 2025 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

Check availability on The Berkshires Romantic Hotels

Tonight

Tomorrow

This weekend

Next weekend

Top Romantic Hotels in The Berkshires

Step into the charming Shaker Mill Inn, surrounded by lush greenery and a beautiful garden.

"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!"

includes taxes & fees

30 Jul - 31 Jul

Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

"Great stay with all plenty of things to do…"

includes taxes & fees

18 Aug - 19 Aug

Dine in style with a long table set for a memorable meal, surrounded by cushioned chairs and large windows offering a view of the outdoors.

"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. "

includes taxes & fees

17 Aug - 18 Aug

"excellent stay!! The Dewey is a cozy getaway location!"

includes taxes & fees

13 Aug - 14 Aug

Escape to a secluded cabin nestled among the trees, offering a peaceful retreat in the heart of nature.

"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...

Stately building with a neoclassical facade, featuring a central entrance and columns, set amidst a well-manicured lawn.

"Memorable. A wonderful hotel I every aspect. Faultless service from Scoyt and the team"

Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

"Great breakfast, friendly helpful staff, pretty yard, good location "

includes taxes & fees

4 Aug - 5 Aug

Steps lead down to the tranquil lake's edge, surrounded by trees and a rustic stone wall.

"A good place for vacation that you can enjoy and rest. Very nice and safe place."

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"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. "