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

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Check availability on Stockbridge Luxury Hotels

Tonight
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Stockbridge luxury hotels

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.
NT$10,577
NT$12,795 total
includes taxes & fees
Aug 31 - Sep 1
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
NT$12,076
NT$14,164 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge

3. Devonfield Inn B&B

Devonfield Inn B&B
Lee
NT$12,461
NT$13,919 total
includes taxes & fees
Sep 3 - Sep 4
Devonfield Inn B&B

4. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
NT$7,611
NT$8,502 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Terrace Inn

5. 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$2,920
NT$3,261 total
includes taxes & fees
Sep 3 - Sep 4
The Central Downtown Inn & Suites

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
NT$10,213
NT$12,324 total
includes taxes & fees
Sep 1 - Sep 2
The Old Inn On The Green

7. 33 Main

33 Main
Lenox
NT$21,229
NT$23,712 total
includes taxes & fees
Aug 31 - Sep 1
33 Main
View all properties

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Place was clean and well equipped, pool and amenities were great too !"
Nyra 3-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
Linda 1-night trip
Posted 9 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"Very nice, clean, good breakfast. Only complaint was that it was very expensive because we booked last minute and it the peak season. I would stay again but not at the price we were charged."
Josephine 2-night trip
Posted 9 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
Sheila 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Only problem was the stairs. I hadn't realized that there was such a long climb to our condo or I would have asked for something a little friendlier to a 75 year old."
Laura 1-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort
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 3 weeks 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 3 weeks 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 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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