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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
22 Oct - 23 Oct
Tomorrow
23 Oct - 24 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for The Berkshires historic hotels

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

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
€201
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.
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.
€221
includes taxes & fees
28 Oct - 29 Oct
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 kitchen with white cabinets, wooden dining table, and chairs. There are hanging pendant lights and a window with a view.
A narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Diane
€434
includes taxes & fees
30 Oct - 31 Oct
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 cozy living room with a stone wall, a fireplace, and a chandelier.
A cozy living room with a stone fireplace, leather sofas, a wooden coffee table, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
€230
includes taxes & fees
5 Nov - 6 Nov
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 living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.
A cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.
A two-story house with a garage, a driveway, and a river in the background.

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
€472
includes taxes & fees
29 Oct - 30 Oct
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 two-story house with a front porch, a small garden, and a mailbox.
A wooden deck with a grill, a table, and chairs.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.

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.
€350
includes taxes & fees
23 Oct - 24 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
A modern kitchen with white cabinets, a large island, and a skylight.
A bedroom with a large bed, a red rug, a bookshelf, and a chair.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.

7. 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
stephen r.
€1,295
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
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Top The Berkshires Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Unique and very thoughtfully thought through. Welcome bottle of wine, welcome drink, and breakfast were great! Wish the bar was open later and breakfast started earlier, but this is a minor thing. Would definitely stay there again."
Jeffrey 1-night trip
Posted 2 hours ago
The Cornell Inn, Lenox & The Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"clean. local walking distances to everything,"
robert 2-night trip
Posted 3 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

10/10 Excellent
"I loved this property. Nice room with fireplace and balcony, great shower, good breakfast, easy parking, and beautiful walking trail behind the hotel."
Barry 2-night trip
Posted 5 hours ago
The Yankee Inn
Hotel On North

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."
Vicki 1-night trip
Posted 2 days ago
Hotel On North
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean room. Comfortable beds. Good breakfast. Staff were nice and professional."
Melissa 1-night trip
Posted 2 days ago
Hampton Inn & Suites Berkshires-Lenox

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