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

Stockbridge Hotel Guide - Luxury Hotels in Stockbridge, Massachusetts

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Check availability on Stockbridge Luxury Hotels

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Stockbridge luxury hotels

Front of property
The Fox Den in the Mainhouse
Exterior
Exterior

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
€435
includes taxes & fees
23 Sept - 24 Sept
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room
Lobby sitting area
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers
Suite, Private Bathroom (Parlour Suite)

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.
€544
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Exterior detail
Fireplace
Dining
Staircase

3. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
€213
includes taxes & fees
23 Sept - 24 Sept
Hampton Terrace Inn
Front of property – evening/night
Room #10 Queen's Cottage | View from room
Room #4 - Roosevelt Suite, 1 King Bed, Fireplace, not pet friendly
Room #10 Queen's Cottage | Living room

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
€427
includes taxes & fees
23 Sept - 24 Sept
Devonfield Inn B&B
Exterior
Deluxe Double Suite- NO PETS ALLOWED
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.
€95
includes taxes & fees
8 Oct - 9 Oct
The Central Downtown Inn & Suites
Breakfast, lunch, dinner and brunch served
Thayer House, Room 201, 1 King bed, Jetted tub | Living area
Front of property
Interior

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
€347
includes taxes & fees
28 Sept - 29 Sept
The Old Inn On The Green
View all properties

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Our third time there and the kids love it.. is quiet, love the pool and the kids love grilling food and sitting by the fire pit after."
Rosario 2-night trip
Posted 7 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Good place"
Nicholas 2-night trip
Posted 9 hours ago
Quality Inn Great Barrington
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 11 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 17 hours ago
Jiminy Peak Mountain Resort
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 3 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.