Luxury Hotels in Stockbridge, Massachusetts
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Sep 9 - Sep 10Tomorrow
Sep 10 - Sep 11This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Stockbridge luxury hotels
P23,612
P27,694 total
includes taxes & fees
Sep 14 - Sep 15
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 ChesterwoodStockbridge
- Escape to a mountain luxury bed & breakfast where refined elegance meets nature's beauty, just steps from the Norman Rockwell Museum.
P20,680
P25,017 total
includes taxes & fees
Sep 28 - Sep 29
P25,618
P28,615 total
includes taxes & fees
Sep 10 - Sep 11
P20,663
P24,934 total
includes taxes & fees
Sep 21 - Sep 22
P13,711
P15,315 total
includes taxes & fees
Sep 10 - Sep 11
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.
P6,201
P6,926 total
includes taxes & fees
Sep 13 - Sep 14
Top Stockbridge Hotel Reviews
FairBridge Inn Express
10/10 Excellent
"Room was clean and comfortable."
Vacation Village in the Berkshires
10/10 Excellent
"Always a great stay at. Vacation Villages"
The Yankee Inn
10/10 Excellent
"Excellent in every way. Service, staff, amenities. Everything was perfect."
The Black Swan Lee - Lenox, an Ascend Collection Hotel
10/10 Excellent
"Generous front desk (forgot toothbrush & comb, they gave us both free of charge). Great complimentary breakfast & tea/coffee machine. Great WiFi. Beautiful view & kayaking was so fun. We had a wonderful stay!"
Jiminy Peak Mountain Resort
10/10 Excellent
"My family had a wonderful time at Jiminy Peak Mountain Resort! The staff truly cared about making sure we had a great stay. When we had a last-minute change and needed to upgrade our room, they handled everything so seamlessly and were incredibly accommodating. The space we received was much larger than we expected, with four floors, three bedrooms, two bathrooms, and three pull-out sofas. There was more than enough room for our whole family to stay comfortably, and it was very affordable for the amount of space and amenities we received. They were also very generous with towels and blankets. Although we didn’t end up using everything, it was reassuring to know that plenty was available if we needed more. The view from the backyard was beautiful, and the resort attractions were only minutes away. We especially enjoyed the scenic chairlift ride and mountain coaster. Everyone in our family, from old to young, had a great time. Overall, it was a wonderful and very affordable family getaway. We really appreciated the hospitality, spacious accommodations, beautiful surroundings, and activities for all ages. We would definitely recommend Jiminy Peak Mountain Resort!"
Quality Inn Lee - Lenox South
8/10 Good
"Very clean property with kind staff. Nice room, decent complimentary coffee, breakfast offerings not for me."
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."