From cheery multi-level homes overlooking idyllic lakes to modern chateaus on charming cul-de-sacs, we have the perfect accommodations for your next visit to historic Annapolis. Our 6-bedroom vacation homes sleep 12-14 adults in comfort and style. Each comes fully furnished with comfortable and contemporary sofas, love seats, loungers and more, with stylish décor and tasteful accents throughout. You and your family will feel perfectly at home thanks to spacious living rooms with big screen TV’s or home theaters, dens featuring fireplaces and mini-bars, and private bedrooms with en suite bathrooms and large walk-in closets. Our larger vacation home rentals in Annapolis, MD boast spectacular outdoor areas, perfect for entertaining. Stroll the landscaped grounds, enjoy a refreshing drink in Adirondack chairs by the water’s edge, or host a cookout on your backyard patio or 2nd floor covered porch. Here, the options are endless – and they are all yours.
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The Top Vacation Rentals in Annapolis Area
All of our vacation home rentals in Annapolis, MD are individually owned and professionally managed to ensure that we can provide you with the ultimate home away from home. Master suites (our 6-bedroom houses often feature multiple) include indulgent walk-in closets, modern and upscale bathrooms, and beautiful views of Annapolis’s historic downtown or the scenic waterways. Guest bedrooms feature king or queen size beds and plenty of space and privacy, with high-end linens, free Wi-Fi, and charming accents to make you feel right at home. a private en suite bathroom and large walk-in shower or Jacuzzi tub.
While we feature a variety of different floorplans ranging from split-level townhouses to riverside mansions, all of our large vacation rentals in the Annapolis area feature newly renovated kitchens with modern appliances (e.g Bosch, Viking, etc.) and expansive granite countertops, perfect for preparing a family feast. These premium homes also boast luxurious outdoor pools, gardens, themed game rooms, glassed-in solariums, and private docks with slips available for your boat. Nowhere else can you find this incredible combination of value, luxury, comfort, and convenience.
Large Group Adventures
Even though you may feel as if you never want to leave the boundaries of your 6 bedroom vacation rental, you probably should get out and explore, even if you may be worried about finding activities that your entire group can enjoy. One of the many great things about Annapolis is knowing there is something for everyone to do in groups or alone.
Sometimes it’s the little things that make the largest impact, so stopping at the Annapolis Ice Cream Company at 196 Main Street is a tradition enjoyed by visitors and residents alike. Pick your sweet treat from a seemingly endless list of flavors, then take it outside to be enjoyed as you explore the treasures that can be found on Main Street, the hub of Annapolis’s shopping. Offering everything from museum stores to chic boutiques, you could probably spend an entire day on this street alone, wandering in and out of the stores.
A L Goodies General Store at 112 Main Street is home to a fantastic collection of souvenirs and gifts all laid out in a setting that was popular decades ago. Pick up some postcards, Christmas decorations, kitschy socks, or satisfy your sweet tooth with candy from the bins that in another century would have been considered penny candy.
Capital Comics, found at 207 Main Street, may not have anything specific to do with Annapolis or Maryland, but if your family is anything like ours, a comic book store should never be passed by! Our second favorite hobby is reading, and Back Creek Books at 194 Main Street is our own personal slice of heaven. Housed in a historic red brick building, the books they sell here aren’t new; their collection of rare and antique books is extensive, and we want them all!
Dinnertime
As you meander in and out of shops on Main Street, at some point you’re going to be hungry, and fortunately for you, you won’t need to leave the cobbled stone street to find a good restaurant! Mason’s Famous Lobster Rolls is a must for any seafood lover, and being as it can be found at 188 Main Street, your lobster craving will soon be satisfied! Francophiles will adore the French dishes served at Café Normandie on 185 Main Street, and those with a hankering for Mexican will find the dishes served at Vida Taco Bar on 200 Main Street will be exactly what they were hoping for. There’s a meal for every appetite on Main Street in Annapolis!
We are proud to offer more than just the best selection of vacation rentals in the Annapolis area: We offer your dream home away from home. Come explore all the charm, history, and attractions our beautiful city has to offer and let us provide you with the absolute best vacation possible. Our local experts are standing by to help, or you can browse our wide selection of vacation home rentals in Annapolis, MD on our website.
