Find Hotels with a Pool in The Berkshires, MA

    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
30 Apr - 1 May
Tomorrow
1 May - 2 May
This weekend
2 May - 4 May
Next weekend
9 May - 11 May

Compare The Berkshires Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Quiet. Good cleaning "
The price is AED 393
AED 439 total
includes taxes & fees
4 May - 5 May
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, (1802)
"Great property"
The price is AED 434
AED 516 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (778)
"Friendly staff "
The price is AED 364
AED 406 total
includes taxes & fees
28 May - 29 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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, (697)
"Stayed a week while working in the area. Staff was super friendly, rooms were clean & quiet, mattresses pretty comfortable. The only thing keeping it from a solid 5 stars was the breakfast is not so good. Watery eggs just aren't my jam. "
The price is AED 555
AED 620 total
includes taxes & fees
26 May - 27 May
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)
"Very nice and funky place! Clean, friendly nice staff. Have already stayed here twice and plan to stay again!❤️"
The price is AED 465
AED 520 total
includes taxes & fees
1 May - 2 May
Hotel Downstreet, Ascend Hotel Collection
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (538)
"Good location. Easy check in "
The price is AED 427
AED 468 total
includes taxes & fees
13 May - 14 May
Berkshire Valley Inn
Club Wyndham Bentley Brook
Exterior

Club Wyndham Bentley Brook

3.0 star property
9.2 out of 10, Wonderful, (520)
"It's very quiet "
Club Wyndham Bentley Brook
Berkshire Inn
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (765)
"The location is convenient for the Pittsfield area and the room was very comfortable. "
The price is AED 313
AED 349 total
includes taxes & fees
1 May - 2 May
Berkshire Inn
Lantern House Motel
Exterior

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
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"The elevators were not working during our stay. We were notified ahead of time and had an opportunity to cancel the reservation. Despite room being on the second floor, it was not a hardship. The cleanliness of the room, free breakfast and pleasant staff outweighed the inconvenience."
The price is AED 537
AED 600 total
includes taxes & fees
19 May - 20 May
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.
Don't see what you're looking for?
See all available properties in The Berkshires