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

The Berkshires Hotels with Adjoining Rooms

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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 connecting rooms

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 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.

2. 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.

3. 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 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.

4. 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 spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

5. Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 star property

Downtown Great Barrington

8.6 out of 10, Excellent, (1,003 reviews)

8.6/10

Excellent

(1,003 reviews)

"Our room was spotless and the staff was helpful and welcoming!"

Lynne

The price is RM307

RM307

RM343 total

includes taxes & fees

29 Nov - 30 Nov

Quality Inn Great Barrington

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.

6. 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

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.

7. 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

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

3.0 star property

Great Barrington

9.4 out of 10, Exceptional, (821 reviews)

9.4/10

Exceptional

(821 reviews)

"Nice view and location for fall color."

The price is RM652

RM652

RM728 total

includes taxes & fees

12 Nov - 13 Nov

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

A hotel patio with outdoor seating and a fire pit.

A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

A spacious living room with a large sofa, a coffee table, and a fireplace.

9. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property

Pittsfield

9.2 out of 10, Wonderful, (716 reviews)

9.2/10

Wonderful

(716 reviews)

"Great place to stay. Great staff and convenient location. Nice restaurant as well."

James

The price is RM482

RM482

RM538 total

includes taxes & fees

15 Nov - 16 Nov

Hilton Garden Inn Lenox Pittsfield

A straw hat, sunglasses, and two drinks on a striped towel by a body of water.

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

A covered porch with wicker furniture and hanging flower baskets.

10. The Red Lion Inn

The Red Lion Inn

3.5 star property

Stockbridge

8.8 out of 10, Excellent, (1,010 reviews)

8.8/10

Excellent

(1,010 reviews)

"Great location - hotel has an excellent dining room and there are several other restaurants within easy walking distance from hotel. A historic, old hotel with lots of curated artwork and history."

Lisabeth

The price is RM639

RM639

RM916 total

includes taxes & fees

12 Nov - 13 Nov

The Red Lion Inn

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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The Berkshires Hotels with Adjoining Rooms

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires hotels with connecting rooms

1. The Yankee Inn

2. Hotel On North

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

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

5. Quality Inn Great Barrington

6. The Cornell Inn, Lenox & The Berkshires

7. Hampton Inn & Suites Berkshires-Lenox

8. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

9. Hilton Garden Inn Lenox Pittsfield

10. The Red Lion Inn

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