Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
Jul 28 - Jul 29
Tomorrow
Jul 29 - Jul 30
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top The Berkshires Romantic Hotels

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

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 NT$5,477
NT$6,008 total
includes taxes & fees
Jul 30 - Jul 31
Shaker Mill Inn
Vacation Village in the Berkshires
Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

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 NT$2,558
NT$3,180 total
includes taxes & fees
Aug 25 - Aug 26
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

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 NT$3,622
NT$4,045 total
includes taxes & fees
Aug 4 - Aug 5
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Dewey
Exterior

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 NT$6,065
NT$6,775 total
includes taxes & fees
Aug 25 - Aug 26
The Dewey
Chestnut Lodge
Escape to a secluded cabin nestled among the trees, offering a peaceful retreat in the heart of nature.

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

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

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 NT$11,550
NT$13,972 total
includes taxes & fees
Aug 11 - Aug 12
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Ponds at Foxhollow
Steps lead down to the tranquil lake's edge, surrounded by trees and a rustic stone wall.

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
Relax by the serene pool surrounded by lounge chairs and umbrellas.

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 NT$5,859
NT$7,860 total
includes taxes & fees
Aug 25 - Aug 26
The Red Lion Inn
Hilton Garden Inn Lenox Pittsfield
Relax on the patio with wicker sofas and armchairs, surrounded by a fire feature and a beautiful garden view.

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 NT$6,061
NT$6,771 total
includes taxes & fees
Aug 24 - Aug 25
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was lovely."
Home 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires