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

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Check availability on Stockbridge Luxury Hotels

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Stockbridge luxury hotels

View from room
Outdoor pool
Lobby sitting area
Breakfast area

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$508
includes taxes & fees
7 Sept - 8 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Exterior
Exterior
Room

2. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
S$562
includes taxes & fees
15 Sept - 16 Sept
The Inn at Stockbridge
Front of property – evening/night
Living room
Front of property – evening/night
Room

3. Devonfield Inn B&B

Devonfield Inn B&B
Lee
S$552
includes taxes & fees
3 Sept - 4 Sept
Devonfield Inn B&B
Exterior detail
Dining
Staircase
Lobby sitting area

4. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
S$361
includes taxes & fees
17 Sept - 18 Sept
Hampton Terrace Inn
Exterior
Living area
Room
Exterior

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.
S$129
includes taxes & fees
3 Sept - 4 Sept
The Central Downtown Inn & Suites
Restaurant
Interior
Front of property
Room

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
S$489
includes taxes & fees
1 Sept - 2 Sept
The Old Inn On The Green
Room
Exterior
Restaurant
Room

7. 33 Main

33 Main
Lenox
S$894
includes taxes & fees
31 Aug - 1 Sept
33 Main
View all properties

Top Stockbridge Hotel Reviews

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
"Loved our stay. Breakfast was amazing."
Patrick 1-night trip
Posted 14 hours ago
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"."
Mark 3-night trip
Posted 16 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We come up to the Berkshires every year for Tanglewood and always stay here. The rooms are always clean and the staff friendly and helpful. The rooms have either a full kitchen or kitchenette so at the very least you can have coffee when you wake-up. The fact that Vacation Village is on Brodie Mountain it's quiet and restful."
William 3-night trip
Posted 1 day ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 1 day ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"…."
Tiago 3-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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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