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

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Check availability on Stockbridge Luxury Hotels

Tonight
20 Sep - 21 Sep
Tomorrow
21 Sep - 22 Sep
Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct

Our top choices for Stockbridge luxury hotels

Front of property
Exterior
Lobby
Exterior

1. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
AED 1,564
AED 1,834 total
includes taxes & fees
22 Sep - 23 Sep
The Inn at Stockbridge
Suite, Private Bathroom (RedBird Suite) | View from room
Free daily continental breakfast
Suite, Private Bathroom (Parlour Suite) | Premium bedding, iron/ironing board (on request), WiFi (free)
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers

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.
AED 1,897
AED 2,295 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
Lobby sitting area

3. Hampton Terrace Inn

Hampton Terrace Inn
Lenox
AED 804
AED 898 total
includes taxes & fees
23 Sep - 24 Sep
Hampton Terrace Inn
Front of property - evening/night
Room #10 Queen's Cottage | Living room | Flat-screen TV
Front of property - evening/night
Room #10 Queen's Cottage | View from room

4. Devonfield Inn B&B

Devonfield Inn B&B
Lee
AED 1,612
AED 1,801 total
includes taxes & fees
22 Sep - 23 Sep
Devonfield Inn B&B
Exterior
50-inch flat-screen TV with cable channels, TV, streaming services
Deluxe Double Suite- NO PETS ALLOWED | Iron/ironing board, cribs (surcharge), rollaway beds (surcharge)
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.
AED 360
AED 402 total
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 | Premium bedding, WiFi (free), individually decorated
Thayer House, Room 201, 1 King bed, Jetted tub | Living area | 32-inch TV with cable channels
Front of property

6. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
AED 1,212
AED 1,463 total
includes taxes & fees
22 Sep - 23 Sep
The Old Inn On The Green
View all properties

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Very nice stay. Nice town to stay in."
Wendy L 1-night trip
Posted 1 hour ago
Quality Inn Great Barrington
Hotel On North

Hotel On North

10/10 Excellent
"My husband and I (both architects) loved the very creative way the original building had been converted to a hotel. The interiors were very imaginatively designed, preserving the original wood flooring and high ceilings, incorporating art, old machinery that had been in the paper mill, and an interesting combination of antique furniture. Parking was easy and the hotel location was an easy walk to many places of interest. We enjoyed dinner at the restaurant on the premises--elegant and tasty. Finally, kudos to the very friendly and helpful staff who were always eager to answer our questions, talk about the building's history, or provide an item we needed. Thanks to you all!"
Donna 2-night trip
Posted 2 hours ago
Hotel On North
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

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