Cottages in Hampshire County

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Top Cities in Hampshire County

Amherst Farm Winery is a small family owned winery offering an impressive list of fruity wines. We found this impressive old man on the grounds!

Compare 120 Cottages in Hampshire County with updated reviews, rates, and availability.

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

"Just a nice lake house!!"

AED 1,290 total

includes taxes & fees

19 May - 20 May

"Great hosts who made our stay enjoyable. Very peaceful location. "

"The cottage was adorable and spotless. Minutes to Great Barrington and Butternut and close to other Berkshire ski resorts. My family of 5 was so cozy and had plenty of space. The basement bedroom does get cold, especially the floor so bring your slippers!"

"Beautiful home with a great location in the Berkshires. We had a wonderful time!"

"A great stay in a vintage RR caboose. Thanks to everyone at Trainmasters Inn!"

AED 1,193 total

includes taxes & fees

6 May - 7 May

"Excellent property: would have liked to stay longer. "

"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."

"Property is in excellent condition, just the right amount of space for us. "

"We had a great time. The owner Bill was a great host."

"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

"This property was exactly as advertised and was in a safe and private location. The hosts perfectly accommodated our stay and we cannot be more thankful to them for a fully-functional house that was suitable for the adults and children. It was truly a pleasure to stay at this home."

"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "

"Great stay beautiful property"

"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."

"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...