A person snowboarding down a snowy slope.

Find Historic Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Historic Hotels

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 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 covered porch with wicker furniture and hanging flower baskets.
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 spacious living area with a stone fireplace, comfortable seating, and a dining area.
A living room with a sofa, a coffee table, a TV, and a window with curtains.
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.
AED 397
AED 878 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 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.
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
Diane
AED 841
AED 1,764 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 wall, a fireplace, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A cozy living room with a stone fireplace, leather sofas, a wooden coffee table, 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.
AED 551
AED 986 total
includes taxes & fees
4 Nov - 5 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 room with a large bay window overlooking a lake, a patterned armchair, and a glass table with a decorative bowl.
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
AED 1,031
AED 1,784 total
includes taxes & fees
21 Oct - 22 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 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.

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
21 Oct - 22 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 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.

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 5,397 total
includes taxes & fees
29 Oct - 30 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The old fashioned touches like real glasses in the rooms. The flower selections around the property. The condition of the indoor pool and whirlpool were great.The pond and surrounding land are great. Nicest motor lodge I've been to."
Erin 1-night trip
Posted 1 hour ago
The Yankee Inn
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Hotel Downstream in North Adams was a great location for our overnight get-away to bike the Ashuwillticook Rail Trail. The hotel is right down-town, so we were able to walk to Public for dinner and to Bright Ideas Brewery afterwards, and to Dino's for breakfast in the morning. The room was very large and clean. We had a nice view of downtown and the mountains. Staff was very friendly -- we had a very quick check-in and check-out. Parking is right there and free. All very convenient. The hotel only serves continental breakfast, so we chose to go out, but it's nice that they provide water, coffee, tea and fruit all day long."
Rita 1-night trip
Posted 3 hours ago
Hotel Downstreet, an Ascend Collection Hotel
Hotel On North

Hotel On North

10/10 Excellent
"Well maintained and updated property. Very kind and helpful team."
Michele 1-night trip
Posted 23 hours ago
Hotel On North
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Great place to stay, super friendly staff. All that the Lenox and Lee had to offer isn't far. Will stay again."
Jason 1-night trip
Posted 1 day ago
The Cornell Inn, Lenox & The Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 2 days ago
Quality Inn Great Barrington

Explore a world of travel with Expedia