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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Tonight
Aug 2 - Aug 3
Tomorrow
Aug 3 - Aug 4
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top The Berkshires Romantic Hotels

We don't have any properties that match your exact search

Recommended hotels in The Berkshires

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1923)
"Great stay with all plenty of things to do…"
The price is P5,053
P6,282 total
includes taxes & fees
Aug 25 - Aug 26
Vacation Village in the Berkshires
Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.2 out of 10, Wonderful, (656)
"It's a clean, nice place. And easy to get to the surrounding towns."
The price is P24,669
P27,556 total
includes taxes & fees
Aug 8 - Aug 9
Berkshires Untold
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Beautiful location!"
The price is P7,366
P8,228 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (5)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is P9,344
P10,437 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express & Suites Pittsfield - Berkshires
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (566)
"After coming to Lenox for 15 years, I can easily say this is the best in town. "
The price is P8,841
P9,875 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Lenox Berkshires
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is P7,752
P10,933 total
includes taxes & fees
Aug 27 - Aug 28
The Cornell Inn, Lenox & The Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1002)
"Loved our visit"
The price is P10,993
P14,878 total
includes taxes & fees
Aug 27 - Aug 28
The Red Lion Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (723)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is P8,783
P9,810 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Hotel On North
Food and drink

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (749)
"Staff were excellent and welcoming."
The price is P10,993
P12,279 total
includes taxes & fees
Aug 3 - Aug 4
Hotel On North
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Food was great!"
Emily 1-night trip
Posted 1 day ago
The Red Lion Inn