Annapolis, Maryland


Properties Available 37 properties available
USNA Getaway Overlooking Spa Creek, this updated Annapolis condo is perfectly located amidst the city's vibrant entertainment hub. Known for its delicious seafood, sailing, and shopping - there's something for everyone! Attractions like the U.S. Naval Academy Museum, Quiet Waters Park, William Paca House & Garden, Sparrows Beach, and numerous marin
USNA Getaway (594693)
Annapolis, MD
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 6 guests
Song of River City Bring your family and friends to this riverfront home just a mile from the lively and charming heart of Edgewater. Host warm-weather barbecues thanks to the propane grill available on the waterfront deck, and then enjoy your grilled feast alfresco at the dining area overlooking the water. Your kids will love the spacious backyard
Song of River City (290581)
Edgewater, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Chase Creek Retreat This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits above Chase Creek on a spectacular piece of land surrounded by acres of open space, but just minutes from downtown Annapolis and major routes. Enjoy multiple levels of decks and patios that lead down to a wate
Chase Creek Retreat (290238)
Arnold, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
The Ship's Bridge 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 alfr
The Ship's Bridge (290394)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Boasting acres of lawn, a dock, and plenty of outdoor spaces for you and your loved ones to explore and use, this spacious threestory home is definitely calling your name! Sitting on the shores of the beautiful Severn River, this waterfront home away from home welcomes you with unparalleled water views. Outdoor living is key at KR Beach Club. With
KR Beach Club (291680)
Annapolis, MD
House
Bedrooms 7 bedrooms
Bathrooms 5 baths
Guests 14 guests
Seas The Bay 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 sp
Seas The Bay (579378)
Annapolis, MD
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 10 guests
Anchors Aweigh Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, and the Naval Academy, this historic home is the perfect home base for an exciting and memorable trip to Annapolis! This retreat was built in 1900 and renovated in 2018 with all new furniture (2019). The enclosed and
Anchors Aweigh (291093)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
Thomas Point Tranquility 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 do
Thomas Point Tranquility (290128)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
The Morning Watch Nestled into the coastline of Lake Ogleton off of the Chesapeake, this five-bedroom waterfront home with a pool, spa, and private pier features walls of windows and newly renovated interior and exterior spaces to enjoy your coffee during the sunrise. You are only five miles from historic downtown Annapolis and the US Naval Academy
The Morning Watch (290454)
Annapolis, MD
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 10 guests
Nestled on a treestudded site, this wonderful home is perfect for your family and friends to relax and celebrate. Enjoy your stay by the pool, with a covered pavilion to grill, dine, and play. Or, enjoy family time in the screened sun porch and basement game room. At this home, guests can also expect a great indoor and outdoor space, plenty of park
Magnolia House (290255)
Arnold, MD
House Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Waterside with it All 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
Waterside with it All (290377)
Annapolis, MD
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests
Adventure Annapolis Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water view within 100 yards of the community beach, this spacious and open living design offers a tranquil retreat. Recently furnished with all new furniture and beds, including a king bed on the main floor with an en s
Adventure Annapolis (606857)
Edgewater, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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