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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.
Whether you’re looking for complete Airbnb management services or just help with your Airbnb reservations, South End Hospitality wants to be your trusted partner. With over ten years of experience in the hospitality industry, you can count on us to maximize your profits and take good care of your guests.

Recent Guest Reviews

Great location for a girls weekend.

November 2023
5star rating
Positive: Great location. Nice layout of the home.

Really enjoyed our stay at Drew’s place. Drew had quick…

June 2025
5star rating
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

May 2025
5star rating
Had an excellent stay thanks to Drew’s gracious, friendly and prompt help. Much appreciated!

From booking, communication to the stay was amazing

November 2022
5star rating
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…

May 2025
5star rating
Beautiful house, excellent outdoor space. Highly recommended for a Group get away.

It was out first time in Boston and we loved it

December 2025
5star rating
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…

July 2025
5star rating
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

October 2025
5star rating
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.