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Find Historic Hotels in The Berkshires, MA

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Check availability on The Berkshires Historic Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Mallory
AED 579
AED 829 total
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 living room with a sofa, a coffee table, a TV, and a window with curtains.
An outdoor seating area with a fire pit, tables, and chairs.
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.
AED 357
AED 830 total
includes taxes & fees
27 Oct - 28 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 cozy room with a wooden bench, a small table, and a chair.
A room with a wooden bench, a table, and a door with glass panels.
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
AED 841
AED 1,768 total
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 fireplace, leather sofas, a wooden coffee table, and a chandelier.
A staircase with a stone wall on one side and a wooden handrail on the other.
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.
AED 496
AED 916 total
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 cozy living room with a fireplace, a bookshelf, a dining table with checkers, and a large window with a view of the outdoors.
A living room with a large window, a ceiling fan, a television, a glass coffee table, a patterned rug, and two chairs.
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
AED 1,146
AED 1,931 total
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 wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.
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.
AED 691
AED 1,452 total
includes taxes & fees
28 Oct - 29 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 two-story house with a gravel driveway leading to a garage.
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.

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.
AED 3,269
AED 5,410 total
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

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great"
Sharath 1-night trip
Posted 12 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nice Property clean rooms walked the new footpath out back always enjoy the saltwater pool."
Dan 2-night trip
Posted 12 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"The hotel was clean and pleasant. Staff members were courteous and helpful! Very satisfied with our stay and will consider a future stay here!"
Anne Marie 2-night trip
Posted 15 hours ago
Quality Inn Great Barrington
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Wonderful staff , great location ! Fresh brownies offered at check in , specialty cocktails in the evening , lovely breakfast in the morning:)"
Sandra 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires

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