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

Find Luxury Hotels in Stockbridge, MA

  • 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

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

Our top choices for Stockbridge luxury hotels

Suite, Private Bathroom (RedBird Suite) | View from room

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
  • cleanliness
    Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
The price is ￥53,415
￥64,616 total
includes taxes & fees
Jul 13 - Jul 14
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (370 reviews)
  • cleanliness
    Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
The price is ￥17,310
￥19,335 total
includes taxes & fees
Jul 1 - Jul 2
The Central Downtown Inn & Suites
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
The price is ￥70,577
￥82,777 total
includes taxes & fees
Jul 21 - Jul 22
The Inn at Stockbridge
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
The price is ￥53,387
￥64,422 total
includes taxes & fees
Jun 29 - Jun 30
The Old Inn On The Green
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
The price is ￥67,786
￥75,716 total
includes taxes & fees
Jun 29 - Jun 30
Devonfield Inn B&B
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
The price is ￥47,159
￥52,677 total
includes taxes & fees
Jul 7 - Jul 8
Hampton Terrace Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
The price is ￥115,548
￥129,067 total
includes taxes & fees
Jul 23 - Jul 24
33 Main
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Stockbridge Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Had a wonderful 4 night stay at the Black Swan Inn. Location was great - close to Lenox and on a beautiful lake - I recommend booking a lakeside room."
Stacey 4-night trip
Posted less than an hour ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

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.