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
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…
A beautiful home in a nice quiet area
A beautiful home in a nice quiet area
We had a great stay
We had a great stay! We came in town to tour colleges and it was 20 mins from all
The colleges we toured.
The condo was very clean, and comfortable. I loved the the white linens and towels. Teh felt like new.
The host was very helpful and responsiv…
Very sweet cottage. 20 min walk from the beach and…
Very sweet cottage. 20 min walk from the beach and close to a few restaurants etc on Main Street.
This place was perfect for a girl’s getaway
This place was perfect for a girl’s getaway! So homey, close to a lot of shopping, bars and restaurants. The patio and garden area was like a fairytale! We’ll definitely book again!
We had a wonderful experience
We had a wonderful experience. It was conveniently located and offered parking. Host was responsive to any emails and messages sent to him. Accommodations were clean and comfortable
Wonderful
Wonderful! We loved it, nice location walking distance to T stop, restaurants, and shops. Lovely layout, furniture, and two fireplaces. We would stay again!
It was a lovely well kept place in a great area and Drew was a great host
It was a lovely well kept place in a great area and Drew was a great host!