Find Luxury Hotels in Stockbridge, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Stockbridge Luxury Hotels
Tonight
Aug 15 - Aug 16Tomorrow
Aug 16 - Aug 17Next weekend
Aug 21 - Aug 23In two weeks
Aug 28 - Aug 30Our top choices for Stockbridge luxury hotels
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 ChesterwoodStockbridge
- Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
NT$10,577
NT$12,795 total
includes taxes & fees
Aug 31 - Sep 1
NT$12,076
NT$14,164 total
includes taxes & fees
Sep 14 - Sep 15
NT$12,461
NT$13,919 total
includes taxes & fees
Sep 3 - Sep 4
NT$7,012
NT$7,833 total
includes taxes & fees
Sep 10 - Sep 11
5. The Central Downtown Inn & Suites
The Central Downtown Inn & SuitesPittsfield
- Boutique Berkshire guesthouse features spacious suites, designer interiors, and easy access to cultural sites.
NT$2,931
NT$3,274 total
includes taxes & fees
Sep 3 - Sep 4
NT$10,213
NT$12,324 total
includes taxes & fees
Sep 1 - Sep 2
Top Stockbridge Hotel Reviews
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"lovely balcony, spotless room. lousy breakfast. fabulous staff"
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"The room was a good size and it had a refrigerator which I needed. The only complaint was the breakfast. It was not good at all and they ran out of food and orange juice."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Great hotel for a reasonable price. The only drawback is that they didn’t offer shampoos and body wash like most hotels but otherwise a great value."
The Yankee Inn
8/10 Good
"It was very convenient for an overnight with pool and close to downtown. Affordable. I stayed in the annex so no noise from other guests!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"The room was clean and the beds comfortable. The bathroom was small but nice. Lots of construction in the parking areas but luckily we got a parking space. Staff was friendly and helpful. We ate at the hotel, the food was good."
Jiminy Peak Mountain Resort
10/10 Excellent
"Only problem was the stairs. I hadn't realized that there was such a long climb to our condo or I would have asked for something a little friendlier to a 75 year old."
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"Very lovely beautiful Room and property The outside pool was not available"
FairBridge Inn Express
10/10 Excellent
"Stayed for 2 nights. Room was nice and clean, had shampoo, conditioner, soap, hair dryer. Bed was pretty comfortable. Definitely not bad for the price. Would stay here again."
Frequently asked questions
Explore a world of travel with Expedia
- Hotels with Hot Tubs in Lee
- Golf Hotels in Lanesborough
- Hotels near Bousquet Ski Area
- Hotels with Bars in Pittsfield
- Hotels near Goose Pond Reservation
- Hotels near Walter J. Koladza
- Hotels near National Shrine of the Divine Mercy
- Historic Hotels in Richmond
- Lee Hotels
- Romantic Hotels in Lenox
- Golf Hotels in Pittsfield
- Lenox Hotels
- Hotel Wedding Venues Hotels in Great Barrington
- Hotels near Herman Melville's Arrowhead
- Hotels near Tanglewood Music Center
- B&B in Stockbridge
- Pet-Friendly Hotels in Lee
- South Lee Hotels
- Country Houses in Beartown State Forest
- Family Hotels in The Berkshires
- 4 Star Hotels in Great Barrington
- Inns in Beartown State Forest
- Cheap Hotels in The Berkshires
- Hotels near Tyringham Cobble
- Four Seasons Hotels in Monterey
- Richmond Hotels
- Hotels with an Indoor Pool in The Berkshires
- Family Hotels in Monterey
- 4 Star Hotels in Lenox
- Hotels near Ski Butternut
- Resorts & Hotels with Spas in Great Barrington
- Pet-Friendly Hotels in Pittsfield
- Hotels with a Pool in Great Barrington
- Hotels with smoking rooms in Great Barrington
- Cheap Hotels in Pittsfield
- Hotels near Chesterwood
- Hotels with smoking rooms in Lee
- Guest Houses in Pittsfield Intermodal Transportation Center
- Stockbridge Hotels
- Resorts & Hotels with Spas in Sheffield
- Family Hotels in Sheffield
- Hotels near Furnace Brook Winery at Hilltop Orchards
- Hotels with a Pool in Sheffield
- Hotels with an Indoor Pool in Pittsfield
- B&B in Great Barrington
- Casino Hotels in Great Barrington
- Historic Hotels in Lenox
- Boutique Hotels in The Berkshires
- Great Barrington Hotels
- Hotels with a Pool in Stockbridge
- Hotel Wedding Venues Hotels in Stockbridge
- Hotels with an Indoor Pool in Lenox
- Hotels near Guido's Marketplace
- Ski Hotels in Stockbridge
- Hotels near Mahaiwe Performing Arts Center
- Pet-Friendly Hotels in The Berkshires
- Flights to Alford
- Flights to South Lee
- Flights from Washington (DCA) to Pittsfield (PSF)
- Flights from Charleston (CRW) to Pittsfield (PSF)
- Flights from Houston (HOU) to Pittsfield (PSF)
- Flights from Phoenix (PHX) to Great Barrington (GBR)
- Flights from Bangor (BGR) to Pittsfield (PSF)
- Flights from Walter J. Koladza
- Flights from Lee
- Flights from Sydney (SYD) to Pittsfield (PSF)
- Flights from Portsmouth (PSM) to Pittsfield (PSF)
- Flights from Pittsfield Municipal
- Flights from Denver (DEN) to Great Barrington (GBR)
- Flights to Stockbridge
- Flights from Dallas (DFW) to Great Barrington (GBR)
- Flights from Pittsfield
- Flights from Houston (IAH) to Great Barrington (GBR)
- Flights from Chicago (ORD) to Great Barrington (GBR)
- Visit South Lee
- Visit West Stockbridge
- Mission House
- Visit South Egremont
- Lenox Mountain
- Visit Lee
- Charles H. Baldwin & Sons
- South Lee Vacations
- Norman Rockwell Museum
- Berkshire Botanical Garden
- Lee Premium Outlets
- Pleasant Valley Wilderness Sanctuary
- Visit Housatonic
- Visit Great Barrington
- Animagic Museum of Animation
- National Shrine of the Divine Mercy
- Frelinghuysen Morris House and Studio
- Bousquet Ski Area
- Visit Lenox
- Greenock Country Club