SkyRun Vacation Rentals

Meet Our Team

SkyRun Coastal Maine's Local Destination Experts

Our team is composed of unique individuals with a variety of backgrounds! Our local team has a strong synergy that adapts to the dynamic business environment of vacation rental management. 

Tommy Chambers


Tommy lives by the motto “Carpe Diem… Every Diem!” and it is with great enthusiasm that he is designing a smarter future in property management and real estate. Sailing the Maine coast since 2001, Tommy is a forward-leaning entrepreneur whose roots in Maine, through his wife, go back almost 100 years to the 1920’s on Southport’s famous Dogfish Head overlooking the Sheepscot River. Tommy and his wife, Erika, and their 3 kids also have a summer cottage of their own overlooking Linekin Bay and yet a short walk to Boothbay Harbor. Tommy has managed thousands of homes (more than $1 billion in assets managed over his 20 year career), has the respect as one of the top rental-home professionals all over the world through his experience in leasing to foreign diplomats, his team’s unmatched success in leasing metrics, and his development of the latest proptech app for property management. 

As a member of the Forbes Real Estate Council and recorder of the first land-lease on Mars, Tommy now reaches “forward from the past”, continues to honor his roots yet leads in creating the future of his trade with his team of proptech innovators, property management experts, and caring individuals delivering the promise of “Real Estate with Intelligence” and a commitment to interweave EQ into each communication and every process when serving clients. 

To be featured on the cover of the “Top 100” magazine’s leaders in real estate in the first issue of 2021, you’ll be quick to see Tommy’s sentiment in the article reflects the service he and his team provide: “What we’re doing in property management today is like what Tesla did for the auto industry 10 years ago. We’re using innovation, tech, optimum performance, cool technology infrastructure, and exciting products to improve the quality of property management and bring greater benefits, value, and ROI to our clients and investors.”

Pam Deelsnyder

Partner/Business Development
Pam’s entrepreneurial spirit began nearly 25 years ago when she started her own travel company concentrating on cruise vacations.  She very quickly expanded to designing custom travel itineraries for both individuals as well as groups, all around the globe!
While working with her travel groups, Pam realized there was a market for providing promotional items to such groups.  Therefore, Pam started Deel Promos Marketing, Inc., a full-service, promotional products distribution company.
Pam’s connection to Maine began when her oldest daughter went with her grandmother to Belgrade Lakes at the age of 9.  Pam’s husband, Chris, and his family have been vacationing in Maine since he was a young child.  
Pam, along with her husband Chris, own a home on Long Pond in Belgrade Lakes.  Collectively they have been connected to this region for nearly 30 years.  They enjoy their time at the lake with the extended family and their two-year-old golden retriever, Bradley Cooper, fishing, kayaking, boating, and relaxing around evening bonfires complete with s’mores and listening to the calls of the loons.

Jen Ferris

Partner/Business Admin

Jen is smart, resourceful, and the ultimate professional. Jen is a licensed Realtor and specializes in Embassy-Leasing and transition assistance as well as exemplifying that “care” goes a long way in real estate whether selling a $1 million home or renting a $2,000/month condo.

Jen and her family (4 kids!) are posted here in Virginia through the Canadian Embassy (her husband was assigned to a Canadian cooperative military program with the U.S. joint chiefs of staff in the Pentagon). We’re lucky to have Jen on our team and we’re making plans to keep her on the team long-term!

Justin Reeves

Partner/Operations & Media
Justin lives to travel and explore new horizons. At a young age he traveled throughout Europe and has loved it ever since. He started his own travel clothing company at the age of 19 and has always shown great interest in business as well as entrepreneurship. One of the many places he traveled growing up was Maine. His experience there was unforgettable. Between the fresh air, crystal clear lakes,  beautiful scenery, and of course the famous lobster he knew Maine was a special place.

Justin has been working in property management for the past 2 years and is determined to help create the top vacation rental company in Maine. He is a very social person who loves to meet new people anywhere he can. 

Our SkyRun team lives, loves, works and plays in Maine

We are enthusiastic about sharing all the wonderful experiences that Maine, aka “Vacationland” has to offer! 

Our intention is to set the stage for your magical Maine experience - one that you can truly immerse yourself into while enjoying your SkyRun destination! 

Our creative business culture supports a healthy work-life balance with flexible scheduling and collaboration with a sense of purpose in caring for both our guests and our community.

Unsurpassed Customer Service

Meeting Maine property owners and visiting guests and cultivating the relationships we've already made fills our days with purpose! 

When you contact SkyRun Coastal Maine Vacation Rentals, you are guaranteed to get a warm and friendly response, excited to help you book your vacation, resolve an issue, or give you the inside scoop on how to experience Maine like a local “Mainuh”! Of course, you are welcome to call, or book online as well - all in full confidence that we are here if you need anything!

SkyRun Cleaning and Maintenance

SkyRun homes absolutely sparkle - Light... Bright... Open, and Clean! 

We interview and select trustworthy cleaning and maintenance vendors that have a quality reputation and have reasonable prices - the vendors that serve SkyRun properties are an important part of the value chain in property management and in the local community and they have a great sense of pride and purpose in the work they do! We can work with the homeowners preferred service vendors as long as they are licensed and insured.

We're Hiring!

SkyRun Vacation Rentals is a rapidly growing, multi-destination property and rental management company. We're currently seeking high-quality candidates for these positions. If you're an energetic, initiative taking individual who is interested in a caree in hospitality please send your resume to


Cleaning & Quality Specialist
At SkyRun, our top priority is the quality of our product. The Housekeeping Specialist is responsible for maintaining our clients' homes in pristine cleaning condition and ready for guest stays.


Visitor Satisfaction Specialist
The Inspector servers one of the most important roels at SkyRun. The Inspector carefully and diligently prepares our rental homes in order to ensure guest and owner satisfaction.


Home Protection Specialist
To ensure the upkeep of our clients' rental homes, the Maintenance Technician carries out routine maintenance, exterior care and property repair.

SkyRun Coastal Maine

115 Appalachee Rd,
Boothbay Harbor, ME 04538

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