Annapolis, Maryland
44 properties available
This stunning home was custombuilt for entertaining. It boasts a fantastic outdoor space and quality furnishings indoors.
Inside, a comfy family room awaits for movie nights. The billiards room has entertainment for all ages. Escape to the comfortable sitting room with a good book. The large basement game room boasts game tables, a smart TV, thea
Delightfully adorned with nautical charm and soft furnishings, this centrally-located Annapolis home is well-prepared to host you and yours! Nestle down in absolute comfort when you sit on the oversized sofa in the living room and stream your favorite TV shows and movies. When hunger hits, head for the home's full kitchen where you'll be greeted by
Escape to this stunning five-level house nestled on a quiet and expansive 5-acre property in Annapolis, MD. With decks on every level offering breathtaking views, a pool, putting green, and a dock with four kayaks, this vacation rental is a true oasis for outdoor enthusiasts. Lifejackets are conveniently stored in the garden shed for your safety an
Featuring the most sought-after Chesapeake Bay view, this luxurious newly built waterfront Annapolis retreat is ready for you and your family and friends! The porch and balcony are where you will spend most of your time on the rocking chairs or comfy outdoor couch taking in the Chesapeake Bay. The back patio and gardens offer alfresco dining with a
This gorgeous five bedroom home boasts a screened porch, great interiors, and a guests house.
Inside, there are many areas to escape to or gather in. A warm formal living room has a fireplace and comfy seating. The French doors open onto a large screenedin porch overlooking the pool. The huge lower level recreation room has a sectional and anothe
This vacation getaway is the perfect place for the trip of a lifetime, sitting right by the gorgeous Severn River! You and all your guests can rest easy knowing you'll be within driving distance of Maryland's finest cities, such as Annapolis, Washington DC, and Baltimore. You'll be able to spend plenty of vacation time in the woods of Maryland with
Perfect for family and group gatherings, this darling, three-story home near Severn River is calling your name! There is a beautiful paver patio with a backyard firepit surrounded by a wooded backyard and mature landscaping. Planning on hosting warm-weather barbecues? There is a propane grill available for you! The screened porch off the kitchen (m
Just steps from the stadium, make one of the most charming, custom-built stone historic homes on a private lane your vacation stay. It combines the in-town convenience you desire with the seclusion you often long for. Sporting lovely historical and nautical details throughout, it complements Commissioning Week perfectly, making your stay truly memo
Nestled in a family neighborhood between Fishing Creek and the South River, this Annapolis vacation home is great for groups with children, thanks to the various children's sleeping options. It offers a large heated, saltwater pool, and quality furnishings, while is just minutes outside downtown Annapolis. A quick stroll down the street takes you t
Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great walkability to the area's restaurants, art galleries, shops, parks, and water taxi - fun in the sun is inevitable! On days you don't want to go far from your stay, sit and enjoy the pleasant Maryland weather from the sprawling deck
This newly renovated townhouse with a large backyard is the perfect place for your getaway. Each of the four spacious bedrooms has been beautifully outfitted with your comfort in mind. The open floor plan provides great gathering space with comfy seating and a smart TV, making it the perfect living room space for an afternoon nap or group movie nig
Perfectly located only five miles from the heart of Annapolis, this newly updated, four-story home with great views of Lake Ogleton is perfect for your next family getaway! The neighborhood lends itself to long walks, runs, and bike rides. Explore over two miles of community Bay beaches and watch the wildlife as it passes you by. Outdoor living is
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