The Best Hotel with a Concierge in Stockbridge, MA from ￥16,768 in 2026

A river surrounded by autumn-colored trees and a forested hill.

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Our top choices for Stockbridge hotels with concierge

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

1. The Red Lion Inn

Stockbridge

Stephan

￥24,891

￥35,653 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a brick entrance and a white facade.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

Philippe

￥54,316

￥65,707 total

includes taxes & fees

Nov 6 - Nov 7

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

3. The Yankee Inn

Lenox

Basil

￥15,580

￥17,403 total

includes taxes & fees

Oct 21 - Oct 22

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

A cozy library with bookshelves, a fireplace, and comfortable seating.

A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

4. Berkshires Untold

Lenox

Madhavi R

￥20,572

￥22,979 total

includes taxes & fees

Nov 1 - Nov 2

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

5. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

￥24,249

￥27,813 total

includes taxes & fees

Oct 27 - Oct 28

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

A snack bar with shelves of snacks and a refrigerated display.

A modern cafe with a counter, seating area, and large windows.

6. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Ginger

￥15,012

￥16,768 total

includes taxes & fees

Nov 17 - Nov 18

A dining table with pastries, a coffee pot, and a vase of sunflowers.

A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.

A large, two-story white building with a symmetrical facade, columns, and a central entrance.

7. Granville House

Housatonic

Cynthia

￥40,137

￥44,833 total

includes taxes & fees

Oct 25 - Oct 26

A large, two-story house with a well-maintained lawn and a fence.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Devonfield Inn B&B

Lee

Sebastien

￥58,309

￥65,131 total

includes taxes & fees

Nov 2 - Nov 3

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Top Stockbridge Hotel Reviews

Hotel On North

10/10 Excellent

"Nice property. Female employees were nicer/more helpful than male employees"

Vacation Village in the Berkshires

8/10 Good

"This was our 10 yr celebrating my girlfriend’s birthday at Vacation Village. It’s always a nice escape in the fall season. We usually get the larger “A” rooms as we want the in room jacuzzi. This time I got the same larger room but it was a “C” unit. It was a bit smaller all around. And the bed was a small queen instead of the larger king bed. Overall nice. But I will make sure to ask for an “A” unit next year. It is a great location right across the street from Jiminey Peak."

The Yankee Inn

10/10 Excellent

"Well run and worth it!Hot tub closed for maintenance."

The Red Lion Inn

10/10 Excellent

"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"

Jiminy Peak Mountain Resort

8/10 Good

"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."

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Check availability on Stockbridge Hotel with a Concierge

Our top choices for Stockbridge hotels with concierge

1. The Red Lion Inn

2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. The Yankee Inn

4. Berkshires Untold

5. The Cornell Inn, Lenox & The Berkshires

6. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

7. Granville House

8. Devonfield Inn B&B

9. Hotel On North

10. Berkshire Lake Lodge

Top Stockbridge Hotel Reviews

Hotel On North

Vacation Village in the Berkshires

The Yankee Inn

The Red Lion Inn

Jiminy Peak Mountain Resort

Explore a world of travel with Expedia

Find Hotel with a Concierge in Stockbridge, MA

Change your mind

Treat yourself

Be picky

Check availability on Stockbridge Hotel with a Concierge

Our top choices for Stockbridge hotels with concierge

1. The Red Lion Inn

2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. The Yankee Inn

4. Berkshires Untold

5. The Cornell Inn, Lenox & The Berkshires

6. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

7. Granville House

8. Devonfield Inn B&B

9. Hotel On North

10. Berkshire Lake Lodge

Top Stockbridge Hotel Reviews

Hotel On North

Vacation Village in the Berkshires

The Yankee Inn

The Red Lion Inn

Jiminy Peak Mountain Resort

Explore a world of travel with Expedia