TOP Golf Hotels in The Berkshires for 2026 - 𝗙𝗿𝗲𝗲 𝗖𝗮𝗻𝗰𝗲𝗹𝗹𝗮𝘁𝗶𝗼𝗻 on Select Hotels

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Our top choices for The Berkshires hotels with a golf course

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

A hotel room with two beds, a desk, a TV, and a window with curtains.

A modern bathroom with a large mirror, a sink, and a shower.

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

Great Barrington

Cynthia

S$119

includes taxes & fees

18 Nov - 19 Nov

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

A lakeside dock with kayaks and a covered boat ramp.

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.

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

Lee

Gustavo

S$160

includes taxes & fees

15 Nov - 16 Nov

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

A dining area with a glass table, red walls, and framed artwork.

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.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

S$225

includes taxes & fees

27 Oct - 28 Oct

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

A garden with wooden Adirondack chairs and a stone pathway.

4. Berkshire Mountain Lodge

Pittsfield

Joel

S$152

includes taxes & fees

12 Nov - 13 Nov

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

A hotel room with two beds, a desk, a television, and a dresser.

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.

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

Great Barrington

S$205

includes taxes & fees

2 Nov - 3 Nov

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

A hotel room with a bed, a nightstand with a lamp and phone, a chair, and framed pictures on the wall.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

A modern bathroom with a white bathtub, a showerhead, and a towel rack.

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

S$157

includes taxes & fees

1 Nov - 2 Nov

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

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

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.

7. The Red Lion Inn

Stockbridge

Mallory

S$288

includes taxes & fees

4 Nov - 5 Nov

A garden with a white gazebo, a brick pathway, and various plants and flowers.

A courtyard with stone steps, potted plants, and a small wooden structure.

A spacious living room with a grand piano, a red armchair, and a chandelier.

A two-story wooden cabin with a balcony, large windows, and a covered porch area.

8. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

S$212

includes taxes & fees

25 Oct - 26 Oct

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Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"Staff is awesome and this dog friendly hotel doesn’t feel dirty or different than any other boutique hotel."

Vacation Village in the Berkshires

10/10 Excellent

"Great apartment. Large pool. Comfortable bed. Everything we needed for a great stay."

The Yankee Inn

10/10 Excellent

"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent

"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."

Jiminy Peak Mountain Resort

8/10 Good

"Cuisine bien équipée beau site. Un peu vieillot. La porte du lave vaisselle était brisée mais il fonctionnait tout de même bien. On avait un bac avec sel et poivre et sucre en plus que des filtres et sachets à café. Un beau gros four/air fryer dans la chambre également qui était très pratique. Des couverts pour 6 personnes.Jy retournerais sans hésitation . Le lit était confortable. Les oreillers un peu moins"

FairBridge Inn Express

10/10 Excellent

"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"

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Check availability on The Berkshires Golf Hotels

Our top choices for The Berkshires hotels with a golf course

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

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