Find Luxury Hotels in Stockbridge, MA
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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$11,513
NT$13,928 total
includes taxes & fees
Sep 11 - Sep 12
NT$12,015
NT$14,093 total
includes taxes & fees
Sep 14 - Sep 15
NT$12,399
NT$13,849 total
includes taxes & fees
Sep 3 - Sep 4
NT$7,084
NT$7,912 total
includes taxes & fees
Sep 21 - Sep 22
NT$10,163
NT$12,264 total
includes taxes & fees
Sep 1 - Sep 2
6. 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$3,155
NT$3,525 total
includes taxes & fees
Sep 1 - Sep 2
Top Stockbridge Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
"Very quiet despite being larger area than we thought. Staff at check-in helpful as our card had been corrupted .. manually entered info and we were all set! Enjoyed our balcony very much. lot of fun in the pool !"
The Yankee Inn
8/10 Good
"Almost two hotels in one. Several structures. One nicely updated, all check-ins, breakfast. Our stay was in an older building… while it was clean there was a musty smell. The room was very dated and the ac was loud… Time to upgrade that building."
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
"Fine place to stay in the Lenox area."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"I liked the balcony overlooking the lake"
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."
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."
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- 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
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- Animagic Museum of Animation
- National Shrine of the Divine Mercy
- Frelinghuysen Morris House and Studio
- Bousquet Ski Area
- Visit Lenox
- Greenock Country Club