Find Hotels with a Pool in The Berkshires, MA

Start date: Check-in selected.
To Date
End date: Check-out
    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 a Pool

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
Next weekend
Oct 3 - Oct 5
In two weeks
Oct 10 - Oct 12

Top The Berkshires Hotels with a Pool

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, (2022)
"Clean room, friendly staff, affordable."
The price is ￥14,813
￥18,186 total
includes taxes & fees
Oct 20 - Oct 21
Vacation Village in the Berkshires
Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (662)
"It was a great Stay where we had to it was a good area I would come back to this place again "
The price is ￥13,933
￥18,902 total
includes taxes & fees
Sep 29 - Sep 30
Berkshire Mountain Lodge
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (45)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ￥18,933
￥21,148 total
includes taxes & fees
Oct 2 - Oct 3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
The Yankee, Trademark Collection by Wyndham
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1012)
"Nice area to visit "
The price is ￥17,356
￥19,388 total
includes taxes & fees
Oct 1 - Oct 2
The Yankee, Trademark Collection by Wyndham
Huttopia Berkshires
Outdoor pool

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ￥14,650
￥16,364 total
includes taxes & fees
Sep 29 - Sep 30
Huttopia Berkshires
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1009)
"great place have stayed several times, and hope to return."
The price is ￥24,352
￥33,881 total
includes taxes & fees
Sep 29 - Sep 30
The Red Lion Inn
Element Lenox Berkshires
Indoor pool

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is ￥26,609
￥29,723 total
includes taxes & fees
Oct 5 - Oct 6
Element Lenox Berkshires
Mount Snow Grand Summit Resort
Outdoor pool

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (226)
"Great place to stay!"
The price is ￥21,160
￥25,326 total
includes taxes & fees
Oct 29 - Oct 30
Mount Snow Grand Summit Resort
Blackberry River Inn
Seasonal outdoor pool

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (136)
"Loved everything especially Lucas and Joe💟☮️"
The price is ￥24,569
￥28,254 total
includes taxes & fees
Sep 29 - Sep 30
Blackberry River Inn
Hotel Downstreet, an Ascend Collection Hotel
Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (1012)
"Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool"
The price is ￥21,658
￥24,193 total
includes taxes & fees
Oct 27 - Oct 28
Hotel Downstreet, an Ascend Collection Hotel
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.
View all properties

Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"It's just a nice place and the staff is very nice "
Robin 5-night trip
Posted 4 days ago
The Yankee, Trademark Collection by Wyndham

Explore a world of travel with Expedia

Explore a world of travel with Expedia