Photo by Photo courtesy of Berkshire Visitors Bureau

Hotels with parking in The Berkshires, Massachusetts

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Check availability on The Berkshires Hotels with parking

Our top choices for The Berkshires hotels with parking

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is P5,427
P6,061 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Yankee, Trademark Collection by Wyndham

The Nest Hudson

The Nest Hudson
3.5 star property
Hudson
9.6 out of 10, Exceptional, (210)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (817)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is P6,422
P7,173 total
includes taxes & fees
Dec 21 - Dec 22
Berkshires Untold

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1003)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is P5,875
P6,562 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
The price is P6,958
P8,071 total
includes taxes & fees
Dec 22 - Dec 23
Nautical Nest

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (437)
"Nice place, easy check in"
United States
Robert
The price is P6,853
P7,517 total
includes taxes & fees
Dec 21 - Dec 22
Shaker Mill Inn

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (3)
"Really happy with our stay and the way we felt at this hideaway "
United States
Edwin
The price is P9,409
P10,350 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hideaway Inn Mt. Snow

The Whitlock

The Whitlock
2.0 star property
Lenox
8.6 out of 10, Excellent, (281)
"great location"
United States
Brian
The price is P8,221
P9,183 total
includes taxes & fees
Dec 23 - Dec 24
The Whitlock

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is P4,435
P4,954 total
includes taxes & fees
Dec 22 - Dec 23
Best Western Plus Berkshire Hills Inn & Suites

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (591)
"Roomy, clean, the view is fantastic with the foliage, exactly like the photos. "
United States
Mingming
The price is P8,141
P9,094 total
includes taxes & fees
Dec 22 - Dec 23
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