Get To Know Us
Get to know Wayward Venture Management, your gateway to an exceptional Annapolis experience. Our mission is to provide discerning travelers, including midshipmen parents, sailors, and weekend adventurers, with the perfect blend of luxury and convenience. Nestled in the historic district of downtown Annapolis, our meticulously maintained historic home, built in 1900, showcases an Americana exterior with navy blue accents, white trim, and a welcoming red door, creating a warm and inviting atmosphere. Inside, you’ll find comfortable and relaxing high-end furniture and old wood floors on the upper level, seamlessly combining modern comfort with the charm of a bygone era.
Our commitment to your well-being extends beyond aesthetics. Each space is professionally cleaned, offering clean breathable soft linens and Beekman 1802 bath products for your comfort. Rest easy on Helix luxury mattresses, and enjoy restful nights behind blackout curtains. We understand the importance of staying connected, so we provide complimentary high-speed WiFi and a dedicated work space. For culinary enthusiasts, our fully stocked chef’s kitchen awaits your culinary adventures, while the convenience of a full-size washer and dryer ensures you’re prepared for every aspect of your journey. Whether you’re here for leisure or business, our smart lock keyless entry simplifies your stay. And don’t forget our backyard fire pit seating area, a tranquil space to create lasting memories under the Annapolis sky. Welcome to the Restriction Retreat, where your Annapolis adventure begins with exceptional hospitality and unparalleled comfort.
Our Team
At Wayward Venture Management, our key values and mission revolve around crafting an unforgettable Annapolis experience for our guests. Nestled within the historic district of downtown Annapolis, our 1900-built home exudes timeless charm with its Americana exterior, combining navy blue accents, white trim, and a welcoming red door. We take pride in providing a warm and inviting environment, complete with comfortable high-end furniture and the enduring character of old wood floors on the upper level, ensuring each stay is a harmonious blend of modern luxury and historic authenticity.
Our mission extends beyond aesthetics. We are dedicated to offering meticulously maintained spaces, professionally cleaned to the highest standards, adorned with clean breathable soft linens and stocked toiletries for your comfort. With Helix luxury mattresses and blackout curtains, we prioritize your restful nights. We understand the importance of staying connected, which is why we provide complimentary high-speed WiFi and a dedicated workspace. For culinary enthusiasts, our fully stocked chef’s kitchen awaits your creative endeavors, while the convenience of a full-size washer and dryer ensures you’re well-prepared for your Annapolis adventure. Our smart lock keyless entry simplifies your stay, and our backyard fire pit seating area offers a serene space to create lasting memories under the Annapolis sky. Our mission is to provide impeccable hospitality and exceptional comfort, ensuring every guest experiences the very best Annapolis has to offer.
Exceptional Hospitality
We prioritize providing top-tier hospitality to guests of all ages, ensuring an extraordinary experience.
Timeless Charm
Preserving the enduring charm of our historic 1900-built home, where classic Americana meets modern comfort.
Modern Comfort
Elevate your stay with Helix luxury mattresses with GlacioTexTM Cooling cover and are CertiPUR-US(R), blackout curtains, and soft, breathable linens.
Seamless Connectivity
Stay connected with complimentary high-speed WiFi and a dedicated workspace for business or leisure.
Impeccable Cleanliness
Our commitment to cleanliness means professionally cleaned spaces and well-stocked toiletries for peace of mind.
Culinary Exploration
Discover culinary delights in our fully stocked chef's kitchen with Williams Sonoma dinnerware and cookware, designed for chefs of all levels.
Convenient Stay
Simplify your visit with smart lock keyless entry, a full-size washer and dryer, and a central downtown location.
Memorable Outdoors
Create lasting memories in our backyard fire pit seating area, a tranquil oasis beneath the Annapolis sky for gatherings and relaxation.
Get To Know Us
Get to know Wayward Venture Management, your gateway to an exceptional Annapolis experience. Our mission is to provide discerning travelers, including midshipmen parents, sailors, and weekend adventurers, with the perfect blend of luxury and convenience. Nestled in the historic district of downtown Annapolis, our meticulously maintained historic home, built in 1900, showcases an Americana exterior with navy blue accents, white trim, and a welcoming red door, creating a warm and inviting atmosphere. Inside, you'll find comfortable and relaxing high-end furniture and old wood floors on the upper level, seamlessly combining modern comfort with the charm of a bygone era.
Our commitment to your well-being extends beyond aesthetics. Each space is professionally cleaned, offering clean breathable soft linens and Beekman 1802 bath products for your comfort. Rest easy on Helix luxury mattresses, and enjoy restful nights behind blackout curtains. We understand the importance of staying connected, so we provide complimentary high-speed WiFi and a dedicated work space. For culinary enthusiasts, our fully stocked chef's kitchen awaits your culinary adventures, while the convenience of a full-size washer and dryer ensures you're prepared for every aspect of your journey. Whether you're here for leisure or business, our smart lock keyless entry simplifies your stay. And don't forget our backyard fire pit seating area, a tranquil space to create lasting memories under the Annapolis sky. Welcome to the Restriction Retreat, where your Annapolis adventure begins with exceptional hospitality and unparalleled comfort.
Book Your Stay
Our Team
At Wayward Venture Management, our key values and mission revolve around crafting an unforgettable Annapolis experience for our guests. Nestled within the historic district of downtown Annapolis, our 1900-built home exudes timeless charm with its Americana exterior, combining navy blue accents, white trim, and a welcoming red door. We take pride in providing a warm and inviting environment, complete with comfortable high-end furniture and the enduring character of old wood floors on the upper level, ensuring each stay is a harmonious blend of modern luxury and historic authenticity.
Our mission extends beyond aesthetics. We are dedicated to offering meticulously maintained spaces, professionally cleaned to the highest standards, adorned with clean breathable soft linens and stocked toiletries for your comfort. With Helix luxury mattresses and blackout curtains, we prioritize your restful nights. We understand the importance of staying connected, which is why we provide complimentary high-speed WiFi and a dedicated workspace. For culinary enthusiasts, our fully stocked chef's kitchen awaits your creative endeavors, while the convenience of a full-size washer and dryer ensures you're well-prepared for your Annapolis adventure. Our smart lock keyless entry simplifies your stay, and our backyard fire pit seating area offers a serene space to create lasting memories under the Annapolis sky. Our mission is to provide impeccable hospitality and exceptional comfort, ensuring every guest experiences the very best Annapolis has to offer.
Exceptional Hospitality
We prioritize providing top-tier hospitality to guests of all ages, ensuring an extraordinary experience.
Timeless Charm
Preserving the enduring charm of our historic 1900-built home, where classic Americana meets modern comfort.
Modern Comfort
Elevate your stay with Helix luxury mattresses with GlacioTexTM Cooling cover and are CertiPUR-US(R), blackout curtains, and soft, breathable linens.
Seamless Connectivity
Stay connected with complimentary high-speed WiFi and a dedicated workspace for business or leisure.
Impeccable Cleanliness
Our commitment to cleanliness means professionally cleaned spaces and well-stocked toiletries for peace of mind.
Culinary Exploration
Discover culinary delights in our fully stocked chef's kitchen with Williams Sonoma dinnerware and cookware, designed for chefs of all levels.
Convenient Stay
Simplify your visit with smart lock keyless entry, a full-size washer and dryer, and a central downtown location.
Memorable Outdoors
Create lasting memories in our backyard fire pit seating area, a tranquil oasis beneath the Annapolis sky for gatherings and relaxation.
