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

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Check availability on Stockbridge Luxury Hotels

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Stockbridge luxury hotels

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
Rp6.650.681
Rp7.800.410 total
includes taxes & fees
13 Sept - 14 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.
Rp5.824.859
Rp7.046.389 total
includes taxes & fees
28 Sept - 29 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

3. Devonfield Inn B&B

Devonfield Inn B&B
Lee
Rp7.039.158
Rp7.862.687 total
includes taxes & fees
8 Sept - 9 Sept
Devonfield Inn B&B

4. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
Rp3.900.646
Rp4.357.045 total
includes taxes & fees
21 Sept - 22 Sept
Hampton Terrace Inn

5. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
Rp5.821.860
Rp7.025.221 total
includes taxes & fees
7 Sept - 8 Sept
The Old Inn On The Green

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.
Rp1.746.558
Rp1.950.852 total
includes taxes & fees
7 Sept - 8 Sept
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
"Unit was clean and comfortable. Staff was friendly and helpful."
Edwina 2-night trip
Posted 1 hour ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Great location and beautiful views overlooking the lake. A super quick drive to Main Street in Lee or over to Lenox! We didn’t have time to eat at the restaurant but the food looks amazing!"
Sara 2-night trip
Posted 21 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
FairBridge Inn Express

FairBridge Inn Express

8/10 Good
"The exterior is scary. The lobby is a fright. Rooms however were clean and updated. I appreciate that. But the lot is a disgrace."
Janet 1-night trip
Posted 2 days ago
FairBridge Inn Express
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."
Janet L. 2-night trip
Posted 3 days ago
Quality Inn Great Barrington
Hotel On North

Hotel On North

8/10 Good
"Nice room! Comfortable bed. Super friendly staff."
Jana 1-night trip
Posted 6 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 2 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 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.

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