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

Best Luxury Hotels in Stockbridge

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Check availability on Stockbridge Luxury Hotels

Tonight
21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Stockbridge luxury hotels

Front of property
Lobby
Exterior
1 bedroom, premium bedding, laptop workspace, iron/ironing board

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
RM1,738
RM2,038 total
includes taxes & fees
23 Sept - 24 Sept
The Inn at Stockbridge
View from room
Lobby sitting area
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers
Free daily continental breakfast

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.
RM2,108
RM2,550 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail
Dining
Staircase
Fireplace

3. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
RM893
RM998 total
includes taxes & fees
23 Sept - 24 Sept
Hampton Terrace Inn
Front of property – evening/night
Front of property – evening/night
View from room
Premium bedding, iron/ironing board, free WiFi, bed sheets

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
RM1,792
RM2,002 total
includes taxes & fees
23 Sept - 24 Sept
Devonfield Inn B&B
Exterior
Iron/ironing board, cots/infant beds, rollaway beds, free WiFi
Exterior
50-inch flat-screen TV with cable channels, TV, streaming services

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.
RM400
RM447 total
includes taxes & fees
8 Oct - 9 Oct
The Central Downtown Inn & Suites
Breakfast, lunch, dinner and brunch served
Premium bedding, free WiFi, individually decorated
Front of property
Interior

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
RM1,346
RM1,624 total
includes taxes & fees
23 Sept - 24 Sept
The Old Inn On The Green
View all properties

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 4 hours ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 9 hours ago
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excelente A+, lo recomiendo"
Erick 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox

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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