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
Good place to stay, super convenient and walkable
Good place to stay, super convenient and walkable
Except the location is close to car park which is not so suitable for travelers that are very sensitive to
Except the location is close to car park which is not so suitable for travelers that are very sensitive to sound. Otherwise everything is good in terms of cleaningness, convenience, instructions and responsiveness of house owner.
Andrew was great
Andrew was great! Place was beautiful and clean, using environmentally conscious soaps, etc. Surroundings are beautiful. Lots of young college students in the area and when they pass by at night, can be loud talking but I found this delightful. Ener…
Great spot in a great location
Great spot in a great location. Would recommend!
We enjoyed our stay in Drew’s place
We enjoyed our stay in Drew’s place, it was clean and beautifully arranged, the kitchen was stocked with everything you might need, good appliances, even the pots and pans were good quality and like new. Great backyard and comfortable with yard furn…
Drew was an excellent host
Drew was an excellent host. Felt like home. Short walk to the beach, and quick ride to anything you might possibly need. The house had everything from linens to pots and pans, utensils, etc. Well prepared for our stay. Serene peaceful area. We watch…
My second time staying at The Chester and it was great again
My second time staying at The Chester and it was great again! The apartment was clean and bedding is comfortable. Extra room for my college student to stay a few nights while we moved him into his new housing is ideal. Location is perfect for ge…
Great location and property
Great location and property
Great location, updated small studio, very comfortable bed/pillows, and quality linens
Great location, updated small studio, very comfortable bed/pillows, and quality linens.