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 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Stockbridge luxury hotels

A living room with a fireplace, leather sofas, and a dog.
A stone fountain surrounded by trees in a park setting.

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
NT$11,862
NT$13,913 total
includes taxes & fees
Sep 15 - Sep 16
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 dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

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.
NT$11,396
NT$13,786 total
includes taxes & fees
Oct 1 - Oct 2
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 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.

3. Devonfield Inn B&B

Devonfield Inn B&B
Lee
NT$12,870
NT$14,375 total
includes taxes & fees
Sep 17 - Sep 18
Devonfield Inn B&B
A dining area with round tables set for two, a fireplace, and a mural on the wall.
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 cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.
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
NT$10,384
NT$12,530 total
includes taxes & fees
Sep 15 - Sep 16
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 grand staircase with red carpeted steps and a wooden handrail, leading to a landing with a vase of flowers and a framed picture.
A room with a grand piano, a chessboard, a horse statue, and a blue armchair.
A traditional living room with a fireplace, a grand piano, plush seating, and a bookshelf.

5. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
NT$7,392
NT$8,257 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Terrace Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.
A hotel room with two beds, a nightstand with a lamp, and a window with curtains.
A compact living space with a kitchenette, a dining area, and a sofa.
A modern apartment with a living room, kitchenette, and dining area.

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.
NT$3,115
NT$3,480 total
includes taxes & fees
Sep 17 - Sep 18
The Central Downtown Inn & Suites
View all properties

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Beautiful location and views. Spacious room with all amenities."
Sherry 1-night trip
Posted 15 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
Joanne 2-night trip
Posted 2 days ago
The Yankee Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Kimberly 2-night trip
Posted 2 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 3 days ago
Jiminy Peak Mountain Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
Mary 1-night trip
Posted 3 days ago
Quality Inn Lee - Lenox South
Hotel On North

Hotel On North

10/10 Excellent
"Best place in town"
Mary Ellen 2-night trip
Posted 4 days ago
Hotel On North
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

10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
Lisa 1-night trip
Posted 3 weeks ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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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