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 23 - Aug 24Tomorrow
Aug 24 - Aug 25Next weekend
Aug 28 - Aug 30In two weeks
Sep 4 - Sep 6Our 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$10,519
NT$12,725 total
includes taxes & fees
Sep 7 - Sep 8
NT$12,010
NT$14,086 total
includes taxes & fees
Sep 13 - Sep 14
NT$12,393
NT$13,843 total
includes taxes & fees
Sep 3 - Sep 4
NT$7,149
NT$7,985 total
includes taxes & fees
Sep 21 - Sep 22
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$3,193
NT$3,566 total
includes taxes & fees
Sep 1 - Sep 2
NT$10,157
NT$12,256 total
includes taxes & fees
Sep 1 - Sep 2
Top Stockbridge Hotel Reviews
Quality Inn Great Barrington
10/10 Excellent
"A nice little hotel. Friendly staff. Well-maintained. And the nice thing is the location - it's in downtown Great Barrington, so you can walk to restaurants and other attractions without having to get into your car. No more than 30 minutes from Tanglewood, Shakespeare and Co., and Jacob's Pillow. Also a 20-minute walk from a small lake and beach."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Vacation Village in the Berkshires
8/10 Good
"Price - quality =awesome"
FairBridge Inn Express
10/10 Excellent
"It was very nice and everyone was extremely helpful"
Howard Johnson by Wyndham Lenox
8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
10/10 Excellent
"My stay at Diane’s bed and breakfast was absolutely wonderful. Diane herself is incredibly warm, welcoming, and genuinely informative — she made the entire experience feel personal and cared for. The room was quaint, cozy, and charming in that classic New England way, with comfortable beds, plenty of towels, and a generous selection of bath amenities that made settling in effortless. Breakfast was a standout: a truly amazing cook‑to‑order meal that felt both homemade and high‑end. Every dish was fresh, delicious, and clearly prepared with pride. Parking was plentiful and convenient, making arrival and departure stress‑free. Overall, this B&B is a gem — comfortable, inviting, and thoughtfully run. I’d happily return and recommend it to anyone looking for a relaxing stay."
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