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Historic Hotels & Resorts in The Berkshires from NZ$365

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Check availability on The Berkshires Historic Hotels

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 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 bar with wooden floors and shelves filled with bottles.
A backyard with a swimming pool, lounge chairs, and a hot tub.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Patricia
NZ$365
includes taxes & fees
8 Sept - 9 Sept
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 two-story building with a swimming pool, outdoor seating, and a sign for 'John Harvard's Restaurant & Brewery'.
A snow-covered outdoor area with a fire pit, tables, and chairs, surrounded by buildings and a ski lift in the background.

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.
NZ$410
includes taxes & fees
1 Sept - 2 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 narrow hallway with a wooden floor, a black door at the end, and a wall with floral wallpaper.
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.

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
NZ$805
includes taxes & fees
17 Sept - 18 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 bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.
A cozy living room with a stone wall, a fireplace, and a chandelier.
A staircase with a stone wall on one side and a wooden handrail on the other.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
NZ$411
includes taxes & fees
8 Sept - 9 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 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
NZ$858
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 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.
NZ$661
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 spacious living area with a fireplace, a dining table, and a kitchen area with wooden cabinets and a stove.
A cozy interior with a fireplace, wooden walls, and a chandelier.

7. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
NZ$562
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space
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 cozy living room with a stone fireplace, a blue sofa, and a mounted deer head.

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.
NZ$2,404
includes taxes & fees
22 Sept - 23 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
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Top The Berkshires Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Stacia 1-night trip
Posted 12 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great visit to Stockbridge. Can't think of a better place to stay than the iconic Red Lion Inn."
Daniel 2-night trip
Posted 1 day ago
The Red Lion Inn
The Little Lion

The Little Lion

8/10 Good
"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."
Bruce 1-night trip
Posted 1 day ago
The Little Lion
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Nice place"
Peter 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Hotel On North

Hotel On North

10/10 Excellent
"No comment."
Lauri 1-night trip
Posted 2 days ago
Hotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Fine place to stay in the Lenox area."
Anthony 1-night trip
Posted 3 days ago
Best Western Plus Berkshire Hills Inn & Suites
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 6 days ago
Howard Johnson by Wyndham Lenox

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