The Best Historic Hotels in The Berkshires, MA from AED 830 in 2026

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Our top choices for The Berkshires historic hotels

1. The Red Lion Inn

Stockbridge

James

AED 580

AED 830 total

includes taxes & fees

23 Sep - 24 Sep

Coffee/tea maker, fridge, microwave, oven

2. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock

Kristina L.

AED 383

AED 863 total

includes taxes & fees

9 Sep - 10 Sep

3. A roomy remodeled retreat close to MassMoCA

North Adams

Jennifer O.

AED 841

AED 1,768 total

includes taxes & fees

9 Sep - 10 Sep

2 bedrooms, iron/ironing board, WiFi, bed sheets

4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

Granby

Kristen S.

AED 496

AED 916 total

includes taxes & fees

9 Sep - 10 Sep

5. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Collinsville

Mike

AED 1,146

AED 1,942 total

includes taxes & fees

10 Sep - 11 Sep

6. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Hoosick Falls

Anita T.

AED 691

AED 1,452 total

includes taxes & fees

8 Sep - 9 Sep

Coffee/tea maker, fridge, oven, stovetop

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

7. rural, serene + sophisticated space

Red Hook

BRIAN PATRICK M.

AED 1,055

AED 1,333 total

includes taxes & fees

8 Sep - 9 Sep

4 bedrooms, iron/ironing board, WiFi, bed sheets

8. A Country Lodge Straight Out of the Pages of a Great Novel

Pine Plains

Hessie S.

AED 3,269

AED 5,397 total

includes taxes & fees

7 Sep - 8 Sep

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Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. Our room was very large with a sitting area + TV. Bed room area equally as large, also with a TV. The bathroom was gorgeous with thoughtful touches. On the marble counter was a makeup mirror with a stool so one could sit. Parking lot was in rear of hotel, secure and easy access to the lobby. Staff couldn't have been more accessible and pleasant. Highly recommend this hotel"

Willows Motel Williamstown

10/10 Excellent

"Great little motel that was the perfect stay for a quick overnight trip"

The Red Lion Inn

10/10 Excellent

"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

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Great Barrington Vacations

Find Historic Hotels in The Berkshires, MA

Change your mind

Treat yourself

Be picky

Check availability on The Berkshires Historic Hotels

Our top choices for The Berkshires historic hotels

1. The Red Lion Inn

2. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

3. A roomy remodeled retreat close to MassMoCA

4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

5. Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

6. Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

7. rural, serene + sophisticated space

8. A Country Lodge Straight Out of the Pages of a Great Novel

Top The Berkshires Hotel Reviews

Hotel On North

Willows Motel Williamstown

The Red Lion Inn

Quality Inn Great Barrington

Explore a world of travel with Expedia