About Oaks Inn Annapolis
Located just steps from the historic waterfront, the U.S. Naval Academy, City Dock, and Maryland State House, Oaks Inn Annapolis offers an elegant Black-owned boutique lodging experience in the heart of one of America’s most charming historic cities. This beautifully restored 1930s home blends original architectural character with modern comforts, creating a welcoming retreat for families, reunions, military commissioning celebrations, corporate retreats, wedding groups, and leisure travelers alike.
Owned and operated by The Oaks Hospitality Group, founded by Sharon and Quinton Wilder, the property reflects a commitment to exceptional hospitality, community, and inclusive travel experiences. The group also operates boutique lodging and event venues throughout the Washington, D.C. region, offering guests personalized service and thoughtfully curated stays.
Accommodating up to 16 guests, Oaks Inn Annapolis features six spacious bedrooms, multiple gathering areas, a chef’s kitchen, game room, rooftop deck, and an expansive private outdoor patio complete with fire pit, grilling area, and landscaped garden—ideal for entertaining or relaxing after exploring historic Annapolis.
Its unbeatable downtown location allows guests to easily walk to waterfront restaurants, boutique shopping, museums, sailing excursions, and the vibrant culture that has made Annapolis one of Maryland’s premier travel destinations.
Why Stay Here
- Verified Black-owned boutique hospitality experience
- Walk to the U.S. Naval Academy and City Dock
- Historic downtown Annapolis location
- Sleeps up to 16 guests
- Ideal for family reunions, weddings, and group travel
- Spacious outdoor entertaining patio with fire pit
- Multiple indoor gathering and lounge spaces
- Chef’s kitchen and beautifully restored historic home
- Perfect for Commissioning Week, reunions, and retreats
Ownership & Heritage
Oaks Inn Annapolis is owned and managed by The Oaks Hospitality Group, a Black-owned hospitality company founded by Sharon Jackson Wilder, Esq., and Quinton Wilder. The company operates boutique lodging, retreats, event venues, and hospitality experiences throughout Maryland and the Washington, D.C. region while emphasizing inclusive hospitality, community, and exceptional guest experiences.
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