Search Sheffield Cottage Rentals from CA $105

"The best!"

"Absolutely phenomenal "

"Love the place"

"Clean and beautifully decorated room in the coach house overlooking the woods at the rear. Staff were very friendly and helpful and the breakfast delightful. Walkable into Lenox to visit the boutique shops and restaurants. Highly recommend!"

"This “hotel” had so much potential, which honestly made the experience more disappointing. It’s described as a boutique hotel, but in reality it’s more of a refurbished motel with a separate building for the restaurant, lounge, and “front desk.” While the photos make it look charming and thoughtfully designed, in person it felt worn and had an overpowering scent that seemed intentionally pumped into the space. Check-in and check-out were also odd—I only saw someone once, and no one was around when I left. But the biggest issue was the cleanliness. The common areas were noticeably dirty, with unvacuumed rugs, rock salt scattered around, and a general buildup of debris. The back hallway leading to the rooms was even worse—you could feel grit under your feet, and there was potting soil spilled from a plant that clearly hadn’t been cleaned up. The room itself was cuter and somewhat cleaner, though very dark (which made me wonder if that was intentional). The decor had a fun Moroccan-meets-Cuban vibe, which I appreciated. Still, small details—like watered-down hand soap—added to the overall sense of neglect. Overall, I was really bummed. This was meant to be a special anniversary getaway, and while it wasn’t the worst place I’ve stayed, the website feels misleading and the lack of cleanliness overshadowed everything else. It also made me worry that there were other unhygenic things underfoot that just weren't visible."

"Loved everything!"

"We loved our stay at Oak ‘N Spruce. We are an extended family of 15, ranging in age from 3 to 91 years of age, who meet a couple of times a year in the Berkshires. We had 4 units, each with two king bedrooms (one unit was ADA compatible) and it worked out perfectly. We could not believe how much space each unit offered and we were all able to hang out comfortably in one unit. The units, while not new, were very clean and had everything we needed for a long weekend. The indoor pools and the game room were huge hits with the kids. We had a blast and would highly recommend this resort especially to families with children."

"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."

"Standard Courtyard. All was good."