Hotels with Swimming Pool in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with Swimming Pool

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 3 - Oct 5
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Oct 10 - Oct 12

Top The Berkshires Hotels with Swimming 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, (2030)
"Really nice place at a reasonable price"
The price is P5,767
P7,080 total
includes taxes & fees
Oct 20 - Oct 21
Vacation Village in the Berkshires
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 P9,836
P10,987 total
includes taxes & fees
Oct 31 - Nov 1
Element Lenox Berkshires
Berkshire Mountain Lodge
Indoor pool

Berkshire Mountain Lodge

3.0 star property
9.0 out of 10, Wonderful, (668)
"Very convenient set up of both room and kitchen, resort very easy to navigate. "
The price is P6,258
P8,289 total
includes taxes & fees
Oct 2 - Oct 3
Berkshire Mountain Lodge
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1010)
"great place have stayed several times, and hope to return."
The price is P10,418
P14,237 total
includes taxes & fees
Oct 30 - Oct 31
The Red Lion Inn
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, (885)
"Our stay was very pleasant "
The price is P6,076
P6,787 total
includes taxes & fees
Oct 5 - Oct 6
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Mount Snow Grand Summit Resort
Outdoor pool

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (228)
"Great place to stay!"
The price is P8,672
P10,378 total
includes taxes & fees
Oct 29 - Oct 30
Mount Snow Grand Summit Resort
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)
"Very clean, nice amenities , great location!!"
The price is P7,866
P8,786 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Berkshires-Lenox
Knotty Pine
Property grounds

Knotty Pine

2.5 star property
10.0 out of 10, Exceptional, (1)
The price is P8,963
P9,769 total
includes taxes & fees
Nov 1 - Nov 2
Knotty Pine
Hilton Garden Inn Lenox Pittsfield
Indoor pool

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (647)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is P8,151
P9,105 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
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, (1000)
"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 P8,432
P9,419 total
includes taxes & fees
Oct 30 - Oct 31
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.
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Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast."
Eric 1-night trip
Posted 23 hours ago
The Yankee, Trademark Collection by Wyndham

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