Some Vacation Cottages History
Here is a little bit about our story!
In the mid-1970s, Bob and Judy Roe began vacationing on Chincoteague with their four children and quickly fell in love with the island. Their passion for Chincoteague inspired them to leave their careers with the Federal Government, relocate to the island, and open “Roe’s Vacation Services” in partnership with Vacation Cottages.
By the 1990s, Bob and Judy had fully taken over Vacation Cottages, building a family business rooted in hospitality and a love for Chincoteague. In 2012, their youngest daughter, Karen, and her husband, Mike Murphy, continued the legacy by taking over the company, while Karen’s two brothers remained actively involved.
In 2020, Karen and Mike’s youngest daughter, Madison, joined the company with plans to continue the family tradition alongside her husband, Lee Ramsay. Today, their daughter spends her days in the office as part of the fourth generation of Vacation Cottages Rentals, alongside other great-grandchildren of Bob and Judy Roe.
Chincoteague has always been our family’s happy place, and we are proud to carry on the legacy of a family-owned and operated business dedicated to helping others create lasting memories here. We feel incredibly fortunate to work alongside our family every day and continue sharing the place we love most.
“Our secret here at Vacation Cottages, is a guest arrives and a friend returns” -Bob Roe
