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

Find Luxury Hotels in Stockbridge

  • 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 Stockbridge Luxury Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Stockbridge luxury hotels

A two-story house with a brick entrance and a white facade.
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.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

1. 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.
S$491
includes taxes & fees
6 Nov - 7 Nov
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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
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.

2. Devonfield Inn B&B

Devonfield Inn B&B
Lee
S$527
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
View all properties

Top Stockbridge Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"Beautiful boutique hotel. We will be back!"
Rebecca 1-night trip
Posted 2 hours ago
Hotel On North
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Recommend hotel to provide breakfast and extend checkout time to 11 am."
Navaneeth 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"great room and great area"
Ramon 2-night trip
Posted 10 hours ago
Jiminy Peak Mountain Resort
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Room was clean, bed was comfortable, breakfast was good, centrally located for our days events!"
Chuck 1-night trip
Posted 2 days ago
Quality Inn Lee - Lenox South

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 travellers 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm 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.

Explore a world of travel with Expedia