Annapolis Shopping

Whether you are looking for the perfect souvenir, an iconic piece of colonial-era furniture, or simply the latest fashion trends, Annapolis shops and have it all. Plus, no matter which of our comfortable and luxurious vacation rentals you choose to call home during your stay here, you will be conveniently located near incredible shopping areas, perfect for a quick splurge or an extended all-day shopping extravaganza.

A Shopper’s Historic Haven

The historic downtown district is the perfect place to spend a morning (or an entire day) shopping. Whether you are seeking seasonal gifts, eclectic items, or specialty foods, the quaint shops on these winding cobblestone streets will captivate you. In the heart of it all, in the shadow of the Maryland State House, is Maryland Avenue and its array of boutiques, art galleries, and specialty stores. Here you can find Annapolis shops selling every kind of tea imaginable, nautical themed boutiques, antique stores offering quality pieces dripping with history, a vinyl record store (Ka-Chunk Records, 78 Maryland Ave.), and one of the best selections of craft beers and wines (Annebeth’s, 46 Maryland Ave.) around.

High Fashion at Annapolis Shops

Without question, the first stop on your fashion-inspired Annapolis shopping spree should be the consignment shop Navette (88 Maryland Ave) with its incredible selection of designer pieces and an entire line devoted to silk. Just down the block, Dear Annie (65 Maryland Ave) is a cozy boutique that prides itself on unique items, ensuring your outfit will be one of a kind. More high-end stores await on Main St., such as the self-described “funky boutique” Brown Eyed Girl, the costume jewelry paradise of Lou Lou, or the eclectic offerings of the mother-daughter duo who make their own jewelry and offer a wide selection of printed scarves and clothing at Way Off The Beaten Path. Wander the streets, enjoy the rich history and beautiful architecture, and see what hidden gems you discover!


If you prefer it all under one roof, Annapolis is conveniently located close to two world-class malls offering designer names, wide selection, and exceptional prices. The Annapolis Town Centre at Parole was named the city’s best shopping hub for its dazzling array of big box stores, department stores, and fine dining options. Familiar names like Target and Whole Foods mingle with smaller clothing outlets like Anthropologie and south moon under, and ample parking makes a trip here a breeze.

If you are looking for factory outlet bargains on designer goods and apparel, it is just short drive to Arundel Mills in Hannover. The largest outlet mall in the state, it is home more than 200 indoor stores including brand names like Michael Kors, J Crew, Neiman Marcus, and many, many more. Non-shoppers can even spend their time at one of the sports bars or brew pubs while they wait, though we are willing to bet there is a store here for everyone. After all that Annapolis shopping, the family can enjoy a themed dinner show at Medieval Times or head to Dave and Busters for pub food and arcade action.

Clearly, Annapolis has everything you desire when it comes to shopping. We recommend exploring the quaint streets of downtown and strolling the eclectic shops and stands at the City Docks, both of which are conveniently located near many of our rental homes. Visit our listings today to pick out the home and neighborhood to host your visit!

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