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 thoroughly enjoyed our stay during Thanksgiving week to visit our daughters for the holiday
We thoroughly enjoyed our stay during Thanksgiving week to visit our daughters for the holiday. The apartment was sunny and bright with a lot of natural light. The kitchen was well equipped and the furnishings comfortable. The location was great wit…
Great location and lovely interior design
Great location and lovely interior design.
We had a wonderful stay
We had a wonderful stay. There are some really good restaurants near by and train/bus stops where a close enough of a walk so we can get around the city.
Gran opción para visitas de mas de 2 días
Positive:
lo amplio y bien cuidado los detalles , muy bien decorado y amplios espacios
Negative:
todo bien
The house is beautiful – clean and the location is perfect for walking into town or to the lake
The house is beautiful – clean and the location is perfect for walking into town or to the lake. There are great amenities. Highly recommend!
The home was beautiful and property peaceful
The home was beautiful and property peaceful.
Fantastic room, exactly what we were looking for
Fantastic room, exactly what we were looking for. Great communication from Drew! Just wish there was an elevator 😂
Loved every second of staying here
Loved every second of staying here! Drew was super informative prior to arriving, helpful with instructions on self check in. The place itself was spotless, made us feel right at home, it was exactly like the photos & the bed was so comfy (usually I…
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…
Comfortable cottage with everything you need to enjoy the stay!…
Comfortable cottage with everything you need to enjoy the stay! We loved the large outdoor dining space with a fenced in yard and fire pit. Beach is about a mile away but we enjoyed walking there and a few nearby restaurants. Friendly, communicative…