Annapolis, Maryland


Properties Available 45 properties available
This historic home is close to downtown and the stadium, and offers the best location to view the Blue Angels air show! Its conveniently located in the West Annapolis waterfront community and boasts acres of lawn, a dock, a beach, and a beach house. Its surroundings will make for an unforgettable stay on the Severn River. There are many areas to e
Severn River Osprey Cottage (290135)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Tucked away in the 'Windmill Hill' area of Annapolis, this beautiful home is a short stroll to the US Naval Academy, Historic Downtown, or Navy-Marine Corp. Memorial Stadium. This home gives true meaning to Maryland's slogan, Land of Pleasant Living. Completely restored in 2011, the house offers a wide range of amenities. Oriental rugs cover the b
A Stone's Throw (290161)
Annapolis, MD
House
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 8 guests
This home boasts an open floor plan with high-end features and comfortable spaces. This home is just two blocks from the Eastport Bridge and three blocks to City Dock. Enjoy downtown Annapolis convenience and charm with Eastport serenity. Eastport is ripe with fantastic eateries and some of our favorite watering holes. Cross the bridge or grab a wa
Portside (290284)
Annapolis, MD
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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
The Liberty Club (290828)
Annapolis, MD
House
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Experience incredible and memorable indoor and outdoor spaces at this spacious waterfront home! Admire unparalleled Lake Ogleton views from your large backyard, which also is equipped with a fantastic dock 6.5 depth, private hot tub, deck, and a screened porch ready for family game night and crab feasts! Private and comfortable, this home is the pe
Base Camp on the Lake (290403)
Annapolis, MD
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 16 guests
On the quiet Lake Ogleton off of the Chesapeake, this waterfront home with a gorgeous new pool, hot tub, and private pier will be a place for you and yours to relax and make memories. This beautiful Frank Lloyd Wright-inspired contemporary home with plenty of waterfront amenities boasts renovated interior and exterior spaces. The kitchen space ha
The Admiral's Retreat (290205)
Annapolis, MD
House
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
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
Severn View of Serenity (575168)
Crownsville, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
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 waterside dock with a p
Chase Creek Retreat (290238)
Arnold, MD
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 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
Welcome to 193 Duke Of Gloucester St, managed by Vacasa. This corner side of a historic duplex is located in the heart of downtown Annapolis. 3 bedrooms and 2.5 bathrooms with sleeping space for 6. Please review our property photos and our available amenities to make sure this rental is a perfect fit for your needs. We strive to keep this informa
The Corner Courtyard (580262)
Annapolis, MD
House
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, allowing you to explore all the attractions Annapolis offers. Nearby, you'll find popular destinations such as Annapolis City Dock, Rams Head on Stage, and the U.S. Naval Academy Museum. Enjoy strolling along the city's waterfron
Skyline Sanctuary (587055)
Annapolis, MD
House
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
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
Waterside with it All (290377)
Annapolis, MD
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 18 guests

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