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

Stockbridge Hotel Guide - Luxury Hotels in Stockbridge, Massachusetts

  • 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
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for Stockbridge luxury hotels

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
€401
includes taxes & fees
7 Sept - 8 Sept
The Inn at Stockbridge

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.
€346
includes taxes & fees
1 Sept - 2 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. 33 Main

33 Main
Lenox
€712
includes taxes & fees
31 Aug - 1 Sept
33 Main

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
€377
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B

5. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€241
includes taxes & fees
7 Sept - 8 Sept
Hampton Terrace Inn

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
€344
includes taxes & fees
7 Sept - 8 Sept
The Old Inn On The Green

7. 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.
€88
includes taxes & fees
3 Sept - 4 Sept
The Central Downtown Inn & Suites
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

8/10 Good
"Nice location, nice breakfast, but no elevator."
Larry 2-night trip
Posted 8 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Fausto 2-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Need an extra chair in handicap rooms"
Thomas 3-night trip
Posted 3 days ago
Best Western Plus Berkshire Hills Inn & Suites
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Very nice front desk staff-courteous, upbeat, helpful. Room was clean but leftover trash in bin and no ice tray in refrigerator. VERY comfortable bed. Train in middle of the night was a throwback experience to a different age-i liked it but some would be frightened of the noise. Excellent location."
Alan 1-night trip
Posted 3 days ago
Quality Inn Great Barrington
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

8/10 Good
"We had an easy time finding it,close to shopping. Would stay again"
LYNN 1-night trip
Posted 4 days ago
Quality Inn Lee - Lenox South
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Parking"
Wilson 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox
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
"Very lovely beautiful Room and property The outside pool was not available"
John 3-night trip
Posted 9 days ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
Michelle 2-night trip
Posted 11 days ago
FairBridge Inn Express

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.