Experience Upscale Annapolis Living

Restriction Retreat: Historic Luxury in Downtown Annapolis

Experience the Charm of a 1900s Row Home - Where Trouble Checks In
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Welcome to the Restriction Retreat, your gateway to an exceptional Annapolis experience. Situated in the vibrant heart of downtown, our elegant row home stands ready to immerse you in unparalleled comfort and sophistication. At the Academy you would get put on restriction if you were caught relaxing or coming home late, here you don’t have to worry about getting in trouble. This relaxation comes without restraints. Curated for the discerning traveler—be it Alumni back on their old stomping ground, family visiting their midshipman or an adventurer drawn to the historic district’s allure—our exquisitely designed space guarantees an unmatched stay.”

Immerse yourself in the quintessential Annapolis ambiance, where history intertwines with modernity. Our thoughtfully furnished home, dating back to 1900, boasts an Americana exterior with navy blue accents and a welcoming red door, while inside, plush Helix luxury mattresses and blackout curtains ensure restful nights. Stroll to Main Street, the Naval Academy, and St. John’s University, soaking in the vibrant local scene, or unwind in our backyard’s fire pit seating area. Every detail has been carefully considered, from the fully stocked chef’s kitchen for culinary enthusiasts to the dedicated workspace with a printer for the productive traveler. As passionate hosts, we take pride in providing professionally cleaned accommodations, complete with breathable linens, toiletries, and complimentary high-speed WiFi. With a touch of historic charm and the convenience of modern amenities, your time in Annapolis is elevated with the Restriction Retreat.

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Experience Annapolis Elegance

Immerse yourself in the rich history of the district while enjoying modern amenities such as Helix luxury mattresses, blackout curtains, and a fully stocked chef's kitchen.

Seamless Comfort and Convenience

Our meticulously maintained luxury historic home, centrally located in Downtown Annapolis, offers more than just a stay—it offers an experience.

Historic Charm, Modern Flair

Our thoughtfully restored luxury row home, built in 1900, harmonizes the charm of plantation shutters and old wood floors with the convenience of smart lock keyless entry and full-size washer and dryer.

Your Annapolis Oasis

Indulge in the relaxation of professionally cleaned spaces, complete with a fully stocked chef's kitchen and dedicated workspace.

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Immerse yourself in the charm and luxury of Annapolis with an unforgettable stay at our historic luxury row home. Designed for guests who have taste and enjoy the little, including midshipmen family, Alumni, and weekend adventurers, our centrally located retreat offers a seamless blend of comfort and convenience. Explore the vibrant Downtown Annapolis scene, from the nearby Naval Academy to Main Street and local boutiques. Enjoy the freedom of upscale living with modern amenities such as Helix luxury mattresses, blackout curtains, and a fully stocked chef’s kitchen. Unwind in the back patio around our fire pit or embrace productivity in the dedicated workspace, all while relishing the warmth of our thoughtfully designed interiors, where historic character meets contemporary comfort.

Wayward Venture Management invites you to embark on a personalized escape to the heart of Annapolis. Our meticulously maintained home, built in 1900, stands as a testament to both history and modern elegance. Step into relaxation with professionally cleaned spaces adorned with clean, breathable linens and stocked toiletries. Sink into the comfort of Helix luxury mattresses and enjoy uninterrupted rest with blackout curtains. As you explore the city’s hidden gems, know that your oasis awaits—a fully equipped chef’s kitchen, high-speed WiFi, and even a full-size washer and dryer ensure your every need is met. Experience the beauty of Annapolis from our Americana exterior with navy blue accents to the fire pit seating area, creating memories that will last a lifetime.

What We Offer

Luxurious Slumber​

Experience ultimate comfort on Helix luxury mattresses with a GlacioTexTM Cooling cover and are CertiPUR-US(R) and enjoy uninterrupted rest behind blackout curtains in our historic Annapolis retreat.​

Heart of the Action

Immerse yourself in Annapolis's vibrant life with a centrally located luxury home, steps away from Main Street, Naval Academy, and marina.

Effortless Connectivity

Stay connected with complimentary high-speed WiFi, and accomplish tasks with ease in our dedicated workspace.

Culinary Delights

Unleash your inner chef in our fully stocked kitchen with Williams Sonoma dinnerware and cookware, and savor the local flavors in Annapolis's finest restaurants.

Historic Elegance

Transport back in time in our 1900-built home, showcasing an Americana exterior with navy blue accents, white trim, and a charming red door.

Outdoor Serenity

Relax and reconnect in our backyard fire pit seating area, offering a tranquil space to unwind under the open skies of Annapolis.

Things you don't want to miss out during your stay

Why Should You Choose the Restriction Retreat?

Unbeatable Location
Upscale Living, Unmatched Comfort
Modern Convenience
Impeccable cleanliness
Charm and Character
Tailored Outdoor Experience

What our clients say about their experience

Frequently Asked Home Rental Questions

Absolutely! Our luxury historic home is centrally located in downtown Annapolis, within walking distance of Main Street, the Naval Academy, St. John’s University, and the marina, ensuring you’re in the heart of the action.

We take pride in offering upscale living. Enjoy features such as Helix luxury mattresses, blackout curtains, clean breathable linens, and stocked toiletries. Additionally, stay connected with complimentary high-speed WiFi and work efficiently in our dedicated workspace with a printer.

Your comfort and safety are our top priorities. Our spaces are professionally cleaned to the highest standards. If you know anything about the military, you know we love checklists and know how to clean! We ensure that clean, breathable linens and toiletries are provided to make your stay worry-free.

Our 1900-built home embraces the charm of yesteryears with modern comforts. The navy blue Americana exterior, comfortable high-end furniture, old wood floors, and plantation shutters create a cozy blend of historic character and modern luxury.

Absolutely! Our backyard fire pit seating area is a perfect place to unwind and connect with fellow travelers. It’s an ideal space to relax under the open sky, making memories during your stay.

Simplifying your experience is our goal. We offer smart lock keyless entry, allowing you to easily check in without the hassle of physical keys. Your arrival and departure will be smooth and convenient.

Ready for the best Home Rental Experience

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