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Find Historic Hotels in The Berkshires, MA

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Check availability on The Berkshires Historic Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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
Stephan
￥24,917
￥35,692 total
includes taxes & fees
Nov 3 - Nov 4
The Red Lion Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.
A spacious living area with a stone fireplace, comfortable seating, and a dining area.
An outdoor seating area with a fire pit, tables, and chairs.
A two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.

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.
￥18,618
￥39,492 total
includes taxes & fees
Oct 8 - Oct 9
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 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
￥36,223
￥75,975 total
includes taxes & fees
Oct 14 - Oct 15
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
Rachel P.
￥21,354
￥39,426 total
includes taxes & fees
Oct 13 - Oct 14
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 room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.

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
￥49,268
￥83,005 total
includes taxes & fees
Oct 20 - Oct 21
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

6. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
￥54,005
￥106,115 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
A kitchen with dark cabinets, a stainless steel stove, a microwave, and a coffee maker.
A living room with a fireplace, a television, a ceiling fan, a clock, and a window with curtains.
A wooden deck with a grill, a table, and chairs.
A wooden bear statue with a 'WELCOME' sign in front of a garden with various plants and a stone pathway.

7. 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.
￥29,703
￥62,416 total
includes taxes & fees
Oct 20 - Oct 21
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, built-in bookshelves, a bedside table, and a window with curtains.
A bedroom with a large bed, a red rug, a bookshelf, and a chair.
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
stephen r.
￥125,753
￥213,657 total
includes taxes & fees
Oct 16 - Oct 17
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 stay, very clean, super comfortable beds. Will def stay again when in the area."
Julia 2-night trip
Posted 11 hours ago
Hotel Downstreet, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

8/10 Good
"Would go there again but would request to be in the main Inn, they have properties all over the town center that are considered the Inn. That was disappointing. A very unique property and super cute!"
Joanne 1-night trip
Posted 12 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Delightful and charming! When you go to an inn that is over 200 years old you don’t know what to expect and everything was a wonderful surprise. Super clean, stylish, and staff that was warm and friendly. We had what we believe was the smallest room in the Inn, not much over 100 ft.², and it was perfect for a one night stay. The breakfast options were a real treat!"
F. Cole 1-night trip
Posted 21 hours ago
The Cornell Inn, Lenox & The Berkshires
Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 2 days ago
Hotel On North
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 2 days ago
Quality Inn Great Barrington

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