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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Hotels with Swimming Pool

Top The Berkshires Hotels with Swimming Pool

The Yankee, Trademark Collection by Wyndham
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1007)
"Wonderful place to stay"
The price is P7,653
P8,549 total
includes taxes & fees
Sep 8 - Sep 9
The Yankee, Trademark Collection by Wyndham
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1944)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is P6,179
P7,528 total
includes taxes & fees
Aug 28 - Aug 29
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Meeting facility

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (856)
"Consistently a clean room with welcoming staff."
The price is P6,563
P7,331 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Indoor pool

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (724)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is P9,527
P10,642 total
includes taxes & fees
Aug 25 - Aug 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Hotel Downstreet, Ascend Hotel Collection
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, Ascend Hotel Collection

3.0 star property
8.8 out of 10, Excellent, (1000)
"Great location!"
The price is P8,198
P9,158 total
includes taxes & fees
Sep 11 - Sep 12
Hotel Downstreet, Ascend Hotel Collection
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (554)
"Very clean and very nice staff. Breakfast was great"
The price is P9,499
P10,610 total
includes taxes & fees
Aug 17 - Aug 18
Berkshire Valley Inn
Club Wyndham Bentley Brook
Private pool

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (534)
"We loved the suite we stayed in. The shower was small, but the water pressure and water temperature were great. Beautiful area!"
Club Wyndham Bentley Brook
Berkshire Inn
Seasonal outdoor pool

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (794)
"good location....easy access to highlight destinations and downtown"
The price is P5,136
P5,737 total
includes taxes & fees
Aug 14 - Aug 15
Berkshire Inn
Lantern House Motel
Seasonal outdoor pool

Lantern House Motel

2.5 star property
8.2 out of 10, Very Good, (455)
"The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should open the windows. How about I decide that? The room was musty-smelling, and everything was very dated and just didn't feel very clean. There are better options in Great Barrington. This is a place to...
Lantern House Motel
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Great staff! Comfortable bed! "
The price is P8,198
P9,158 total
includes taxes & fees
Sep 1 - Sep 2
Hampton Inn & Suites Berkshires-Lenox
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

Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

10/10 Excellent
"This is an old Holiday Inn that the new owners came and made all modern and fancy, including adding a couple of our calories downstairs. Ample parking, although it was full towards the end of the night. Safe location. They did a really good job revitalizing in this place. "
Paul 1-night trip
Posted 2 days ago
Hotel Downstreet, Ascend Hotel Collection