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The Berkshires Hotel Guide - Historic Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Historic Hotels

Tonight
6 Sept - 7 Sept
Tomorrow
7 Sept - 8 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for The Berkshires historic hotels

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.
A bar with wooden floors and shelves filled with bottles.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
James
€195
includes taxes & fees
30 Sept - 1 Oct
The Red Lion Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A snow-covered outdoor area with a fire pit, tables, and chairs, indicating a winter resort setting.
A living room with a sofa, a coffee table, a TV, and a window with curtains.
A spacious living area with a stone fireplace, comfortable seating, and a dining area.

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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
United States
Kristina L.
€208
includes taxes & fees
7 Sept - 8 Sept
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A kitchen with white cabinets, a wooden dining table, and pendant lights.
A room with a wooden bench, a table, and a door with glass panels.
A cozy room with a wooden bench, a small table, and a chair.
A kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
€408
includes taxes & fees
9 Sept - 10 Sept
A roomy remodeled retreat close to MassMoCA
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.
A staircase with a stone wall on one side and a wooden handrail on the other.
A cozy living room with a stone fireplace, leather sofas, a wooden coffee table, and a chandelier.
A cozy living room with a stone wall, a fireplace, and a chandelier.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
€220
includes taxes & fees
9 Sept - 10 Sept
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A patio with a table and chairs, a grill, and a view of a lake.
A room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
A two-story house with a garage, a driveway, and a river in the background.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.

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

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
United States
Mike
€459
includes taxes & fees
10 Sept - 11 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A wooden deck with a grill, a table, and chairs.
A two-story house with a front porch, a small garden, and a mailbox.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.

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

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
United States
Anita T.
€342
includes taxes & fees
8 Sept - 9 Sept
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.
A loft-style room with a wooden ceiling, exposed beams, and a view of the outside through large windows.
A cozy interior with a fireplace, wooden walls, and a chandelier.
A rustic kitchen with wooden shelves, a gas stove, an oven, and a microwave.

7. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
€313
includes taxes & fees
8 Sept - 9 Sept
rural, serene + sophisticated space
A modern kitchen with white cabinets, a large island, and a skylight.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.
A two-story house with a gravel driveway leading to a garage.

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

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
Hessie S.
€1,262
includes taxes & fees
7 Sept - 8 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
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Top The Berkshires Hotel Reviews

Hotel On North

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"
Penelope 1-night trip
Posted 4 hours ago
Hotel On North
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Great little motel that was the perfect stay for a quick overnight trip"
Kate 1-night trip
Posted 5 hours ago
Willows Motel Williamstown
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Colleen And mark 2-night trip
Posted 1 day ago
The Red Lion Inn
Quality Inn Great Barrington

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."
Janet L. 2-night trip
Posted 4 days ago
Quality Inn Great Barrington

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