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
Great location for a girls weekend.
Positive:
Great location. Nice layout of the home.
Really enjoyed our stay at Drew’s place. Drew had quick…
Really enjoyed our stay at Drew’s place. Drew had quick and responsive communication, was super friendly. The house was amazing – family visited for a week while I was working in the area, so really my only regret is that I didn’t get to spend as…
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help. Much appreciated!
From booking, communication to the stay was amazing
From booking, communication to the stay was amazing. I cannot say enough good things about the location, comfort, responses in questions, and overall home away from home experience. It’s convenient to many local restaurants, the beach, stores and su…
Beautiful house, excellent outdoor space. Highly recommended for a Group…
Beautiful house, excellent outdoor space. Highly recommended for a Group get away.
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…
We found this place To be clean and comfortable It…
We found this place To be clean and comfortable It felt very much like home. We would highly recommend it.
We really enjoyed our stay here
We really enjoyed our stay here. It was lovely and clean and had a real Boston feel to it. It was a good walk to local attractions but this suited us as we like to explore on foot and the restaurant downstairs was really lovely.