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Our Properties
All our properties are owned and managed by us.
Shady Pine
Cheshire, MA
Fully-renovated architectural gem in the heart of the Berkshires
Highland Acres
Lanesborough, MA
Your own Berkshire retreat: a 6-bedroom estate on 4 acres
Eph's End
Williamstown, MA
Magnificent estate, ideal for family gatherings, events, and retreats
Blue Ridge Lodge
West Dover, VT
Spacious 7-bedroom Vermont retreat, 5 minutes from Mount Snow
Norrland
West Dover, VT
Nordic chalet minutes from Mount Snow
Shady Pine
Cheshire, MA
Fully-renovated architectural gem in the heart of the Berkshires
Highland Acres
Lanesborough, MA
Your own Berkshire retreat: a 6-bedroom estate on 4 acres
Eph's End
Williamstown, MA
Magnificent estate, ideal for family gatherings, events, and retreats
Blue Ridge Lodge
West Dover, VT
Spacious 7-bedroom Vermont retreat, 5 minutes from Mount Snow
Norrland
West Dover, VT
Nordic chalet minutes from Mount Snow
Doreen Ruppin
We’re a locally owned vacation rental company managing a collection of homes throughout the Berkshires and Southern Vermont. Our goal is to create places where people can slow down, get together with friends, and create wonderful memories.Doreen, our founder, believes in the human touch and that the little things matter. We work hard to make each stay as comfortable and enjoyable as possible. Each of our homes is uniquely designed to fit the character of the house and its surroundings.We pride ourselves on meticulous upkeep, an exceptional guest experience, and unmatched customer service. We hope you’ll stay with us and have a blast!
What guests say
"We had a really great time! The house is beautiful and unique, the location quiet and peaceful, and it fit the photos perfectly. Doreen was great and helpful, and the hot tub was amazing. Would stay again!"
"We had a wonderful stay! The house was incredibly spacious with a warm, homey feel. Our kids absolutely loved it and are already asking when we can come back, we're hoping to make this an annual tradition. Highly recommend!"
"I had the absolute best experience staying here. Lots and lots of space, a great pool and hot tub, fun games and activities. The hosts went out of their way to help us have the best experience. Absolutely would recommend!"
"By far the most special Airbnb we ever had the pleasure of staying in. The photos do not do this home justice, it is simply gorgeous and very relaxing, with space for our large party without ever feeling cramped. We will truly miss our stay here."
"If you and a large group are looking for a house to book, this is the one. 16 people were here and not once did it feel cramped. The house is massive, pictures undersell it, and it's less than a 10 minute drive to Mt Snow."
"Doreen's place was amazing! My group loved coming back to this house after a long day of skiing to enjoy the hot tub, sauna, and fireplace. The house is stunning and the host is extremely responsive. Would absolutely stay here again."