Hotels with free parking in The Berkshires
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Hotels with free parking
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A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Hotels with FREE Parking in The Berkshires

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your current months are November, 2026 and December, 2026.

November 2026

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Our top choices for The Berkshires hotels with parking

Two Adirondack chairs facing a river with a forested hill in the background.

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A hotel room with a fireplace, a desk, a television, and a poster of a lake scene.

1. The Yankee Inn

The Yankee Inn

2.5 star property

Lenox

9.2 out of 10, Wonderful, (1,002 reviews)

9.2/10

Wonderful

(1,002 reviews)

"The location was good for our trip."

Basil

The price is RM515

RM515

RM576 total

includes taxes & fees

20 Nov - 21 Nov

The Yankee Inn

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

2. Garden Gables

Garden Gables

4.0 star property

Lenox

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Lovely place!"

Eyee

The price is RM530

RM530

RM887 total

includes taxes & fees

9 Nov - 10 Nov

Garden Gables

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A library with bookshelves, a television, and two armchairs.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

3. Hotel On North

Hotel On North

3.5 star property

Pittsfield

9.6 out of 10, Exceptional, (981 reviews)

9.6/10

Exceptional

(981 reviews)

"Very nice hotel"

Philip

The price is RM471

RM471

RM526 total

includes taxes & fees

29 Nov - 30 Nov

Hotel On North

A lodge with a large building and a dock by a lake, surrounded by forest.

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside lodge with a dock, fishing rods, and outdoor seating.

A dining area with large windows, wooden furniture, and a view of a lake.

4. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property

Lee

9.2 out of 10, Wonderful, (1,001 reviews)

9.2/10

Wonderful

(1,001 reviews)

"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"

Gustavo

The price is RM435

RM435

RM486 total

includes taxes & fees

3 Dec - 4 Dec

The Black Swan Lee - Lenox, an Ascend Collection Hotel

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

A covered outdoor area with stone pillars and a view of a road and green hills.

5. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property

Lenox

9.2 out of 10, Wonderful, (688 reviews)

9.2/10

Wonderful

(688 reviews)

"Great stay!"

Vandhana

The price is RM510

RM510

RM569 total

includes taxes & fees

15 Nov - 16 Nov

Courtyard by Marriott Lenox Berkshires

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

6. Berkshires Untold

Berkshires Untold

3.5 star property

Lenox

9.0 out of 10, Wonderful, (1,067 reviews)

9.0/10

Wonderful

(1,067 reviews)

"Very nice place beautiful view"

Brian

The price is RM427

RM427

RM477 total

includes taxes & fees

17 Nov - 18 Nov

Berkshires Untold

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

A buffet with various food items, including omelets and other dishes, displayed in metal serving trays.

A modern hotel lobby with seating areas, tables, and a reception desk.

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property

Great Barrington

8.8 out of 10, Excellent, (854 reviews)

8.8/10

Excellent

(854 reviews)

"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."

Cynthia

The price is RM337

RM337

RM376 total

includes taxes & fees

7 Dec - 8 Dec

Holiday Inn Express Hotel & Suites Great Barrington by IHG

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

A modern living room with a fireplace, comfortable seating, and a large window with curtains.

8. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property

Lenox

9.4 out of 10, Exceptional, (1,003 reviews)

9.4/10

Exceptional

(1,003 reviews)

"Lovely room, comfortable bed and a nice breakfast."

judith

The price is RM690

RM690

RM792 total

includes taxes & fees

9 Nov - 10 Nov

The Cornell Inn, Lenox & The Berkshires

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A modern cafe with a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 star property

Pittsfield

9.2 out of 10, Wonderful, (257 reviews)

9.2/10

Wonderful

(257 reviews)

"The room was clean and well kept, breakfast was amazing!"

Ruth

The price is RM418

RM418

RM467 total

includes taxes & fees

6 Dec - 7 Dec

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property

Lenox

9.0 out of 10, Wonderful, (1,003 reviews)

9.0/10

Wonderful

(1,003 reviews)

"Breakfast was great"

Thomas

The price is RM445

RM445

RM497 total

includes taxes & fees

15 Nov - 16 Nov

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.

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Hotels with FREE Parking in The Berkshires

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires hotels with parking

1. The Yankee Inn

2. Garden Gables

3. Hotel On North

4. The Black Swan Lee - Lenox, an Ascend Collection Hotel

5. Courtyard by Marriott Lenox Berkshires

6. Berkshires Untold

7. Holiday Inn Express Hotel & Suites Great Barrington by IHG

8. The Cornell Inn, Lenox & The Berkshires

9. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10. Hampton Inn & Suites Berkshires-Lenox

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