Hotels with Swimming Pool 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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with Swimming Pool

This weekend
Next weekend

Top The Berkshires Hotels with Swimming Pool

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1915)
"Great stay with all plenty of things to do…"
The price is P4,982
P6,194 total
includes taxes & fees
Aug 25 - Aug 26
Vacation Village in the Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is P9,118
P10,185 total
includes taxes & fees
Jul 31 - Aug 1
Holiday Inn Express & Suites Pittsfield - Berkshires

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1013)
"The Res Lion Inn is a New England classic. "
The price is P11,068
P14,925 total
includes taxes & fees
Aug 25 - Aug 26
The Red Lion Inn

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (534)
"Excellent stay!"
The price is P6,009
P7,993 total
includes taxes & fees
Aug 17 - Aug 18
Berkshire Mountain Lodge

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (209)
"Very nice being right on the mountain. "
The price is P8,118
P9,716 total
includes taxes & fees
Aug 28 - Aug 29
Mount Snow Grand Summit Resort

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (722)
"No complaints at all. Great place to stay!"
The price is P8,660
P9,673 total
includes taxes & fees
Aug 27 - Aug 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Huttopia Berkshires

1.0 star property
The price is P6,996
P7,815 total
includes taxes & fees
Aug 24 - Aug 25
Huttopia Berkshires

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1017)
"Loved the Yankee Inn!"
The price is P9,118
P10,185 total
includes taxes & fees
Jul 31 - Aug 1
The Yankee, Trademark Collection by Wyndham

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 P11,642
P13,004 total
includes taxes & fees
Aug 17 - Aug 18
Courtyard by Marriott Lenox Berkshires
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