A nighttime view of a residential area with houses adorned with holiday lights.

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Check availability on Stockbridge Luxury Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Stockbridge luxury hotels

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
A stone fountain surrounded by trees in a park setting.

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
₩505,756
₩593,188 total
includes taxes & fees
Sep 14 - Sep 15
The Inn at Stockbridge
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 cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
  • Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
₩442,956
₩535,848 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A large, two-story house with a well-maintained lawn and a fence.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
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.

3. Devonfield Inn B&B

Devonfield Inn B&B
Lee
₩548,714
₩612,910 total
includes taxes & fees
Sep 13 - Sep 14
Devonfield Inn B&B
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A white two-story house with a front door, windows, and a chimney.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.

4. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
₩442,728
₩534,239 total
includes taxes & fees
Sep 13 - Sep 14
The Old Inn On The Green
A white house with a balcony, green shutters, and a front door with a decorative glass panel. There are two large flower pots on the steps.
A dining room with a large table set for a meal, surrounded by ornate chairs.
A grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

5. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
₩333,522
₩372,549 total
includes taxes & fees
Sep 16 - Sep 17
Hampton Terrace Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.
A modern apartment with a living room, kitchenette, and dining area.
A compact living space with a kitchenette, a dining area, and a sofa.

6. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
Pittsfield
  • Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
₩131,517
₩146,905 total
includes taxes & fees
Oct 5 - Oct 6
The Central Downtown Inn & Suites
View all properties

Top Stockbridge Hotel Reviews

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Therooms were loud on the lower level."
Sheila 1-night trip
Posted 1 hour ago
Quality Inn Lee - Lenox South
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We have visited vacation village in the berkshires many times.It never disappoints. Looking forward to our next trip. 5 stars"
JOANNA 2-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"The staff was extremely friendly. Did see several areas in the room that were dusty. Stains on the wallpaper and some wallpaper chipping off."
Frank 1-night trip
Posted 1 hour ago
Howard Johnson by Wyndham Lenox
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Nasically a large motel with both an outdoor and indoor pool. A bit tired, but reasonably close to Lenox and to Tabglewood."
Jacob 1-night trip
Posted 16 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
sophia 1-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort
Hotel On North

Hotel On North

10/10 Excellent
"Best place in town"
Mary Ellen 2-night trip
Posted 5 days ago
Hotel On North

Frequently asked questions

Are you looking for a luxury hotel for your stay in Stockbridge?
During your visit, you might want to enjoy the bars which Stockbridge is known for.
What's the best high-end hotel in Stockbridge?
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood is a luxury B&B with a seasonal outdoor pool and a terrace, and it's a popular choice for Expedia travelers looking for an elegant place to stay.
When can I expect good weather in Stockbridge?
Planning for the weather is a good way to make your trip to Stockbridge relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Stockbridge?
Experience all that Stockbridge has to offer when you visit Naumkeag Museum, National Shrine of the Divine Mercy, and Norman Rockwell Museum. If you have extra time while you're in the area, you might want to see Berkshire Botanical Garden and Stockbridge Bowl.

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