Find Romantic Hotels in The Berkshires, MA

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top The Berkshires Romantic Hotels

Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (419)
"Nice stay"
The price is NT$5,633
NT$6,179 total
includes taxes & fees
Aug 12 - Aug 13
Shaker Mill Inn
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1936)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is NT$3,166
NT$3,863 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (852)
"Consistently a clean room with welcoming staff."
The price is NT$3,423
NT$3,823 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (320)
"excellent stay!! The Dewey is a cozy getaway location!"
The price is NT$5,179
NT$5,785 total
includes taxes & fees
Sep 3 - Sep 4
The Dewey
Chestnut Lodge
Property grounds

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
Exterior

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
Business center

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$11,753
NT$14,218 total
includes taxes & fees
Aug 25 - Aug 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"Loved our visit"
The price is NT$5,663
NT$7,664 total
includes taxes & fees
Aug 27 - Aug 28
The Red Lion Inn
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

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$4,672
NT$5,219 total
includes taxes & fees
Sep 7 - Sep 8
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG