Meet the Team
Tyler
Senior Property Manager
Nicole
VP Of Operations
Lucas
Head Of Business Development
Andrew
Founder, CEO
Our team is the foundation of our success, and we’re grateful for every member’s contribution. From our reservations and guest services team to our maintenance crew, more than fifteen dedicated professionals work together to ensure each stay is seamless and memorable.
Currently, they have over 100 single-family vacation rentals, on the Cape, in the Berkshires, and in Boston and manage a portfolio of boutique limited-service hotels with around 150 doors and growing.
Recent Guest Reviews
We had a fabulous time at Drew’s home
We had a fabulous time at Drew’s home. We were able to celebrate our nieces fourth birthday while looking at a view of the sunsetting over the water. It really was spectacular and we would absolutely come back again
Great place for a weekend on the cape!
Great place for a weekend on the cape!
Drew was an amazing host
Drew was an amazing host! He was always available for answering questions and promptly replied to my messages. The Chester is a lovely building and the rental rooms lovingly and carefully restored but also modernized. And, The Chester is located nea…
Lucas’ listing in Great Barrington was perfect for our group of 8 (two families of 4)
Lucas’ listing in Great Barrington was perfect for our group of 8 (two families of 4). It was a short drive to Butternut Ski area and very close to the downtown area with shops and restaurants. Our kids loved the games available in the house as well…
Large home with lots of space located in a very…
Large home with lots of space located in a very nice community. Would book again!
We really enjoyed our stay at The Chester
We really enjoyed our stay at The Chester. Beautifully decorated and very clean. Close to many restaurants, stores and Northeastern U where our daughter attends.
It was out first time in Boston and we loved it
It was out first time in Boston and we loved it! Staying at the Chester made our stay memorable. Drew was a great host, super responsive and helpful whenever we asked for recommendations or questions. Highly recommend staying here, the place is even…
The place was great, so close to Fenway and walking distance to great restaurants and services
The place was great, so close to Fenway and walking distance to great restaurants and services. Highly recommend for a trip to Boston, especially for going to Fenway.