Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...

Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...

Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The...

Charming Annapolis home, just 150 feet from the water, with floor to ceiling windows overlooking the expansive waters of the Chesapeake Bay. Water views from almost every room. Features 4 bedrooms and 4 bathrooms with luxury upgrades, viking kitchen appliances, comfortable couches for sleeping...

Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around...

Enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life!! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50 and mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities...

The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms...

A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and...

Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden...

located in a safe residential neighborhood with free parking. We are close to shopping, restaurants and the Chesapeake Bay; just minutes drive to the naval academy and downtown Annapolis. Our space is super clean, super spacious, and super comfortable! We are committed to providing you a great...

Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of...

We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former ' Home of the Week' in the Capital Gazette it is also one of the most...

Our home is centrally situated within the heart of the Historic District. You'll be only ~two blocks from Academy Gate Three, City Dock, St John's College, Main Street food, PACA House weddings and the Maryland state Capital. This is a Federal style, 1870's three-story row home which was partially...

This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...

Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking...

Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space and an expensive way to travel....

Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...

This is an outstanding home for Alumni Weekends, Weddings, Academy Events, or Family Vacations. This beautifully appointed home offers you an at-home setting in the heart of Annapolis! The home in the downtown historic district was completely renovated and expanded in 2006. Park your cars in...

HOUSE This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...

Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...

This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...

Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and...

This beautiful 3br home on the peninsula in Eastport is perfect for your Annapolis visit. It is within walking distance to popular attractions including local and national restaurants, Naval Academy, downtown Annapolis, Annapolis Yacht Club, Eastport Yacht Club, Maritime Museum, Mears Marina,...

Experience the East Coast like never before at this charming 4-bedroom, 2-bathroom vacation rental house in Annapolis! With enough space to sleep 8, this 1,700-square-foot abode boasts a tastefully furnished interior with a gourmet kitchen, in-unit laundry machines, an entertainment system, and a...

The PupPad is an amazing space with even better views. Listen to the soft clank of the sailboat masts in the breeze and watch the sunlight dance on the water. We have fresh herbs growing on the balcony and more fresh air blowing in off the bay that you seldome need the A/C! Come enjoy some time...

Come play with the Big Dawgs on Ego Alley of Naptown! This lofty apartment is in the HEART of Annapolis with easy access to everything. VERY few folks can wake up to the view of Ego Alley (The Annapolis Waterfront) and enjoy an amazing morning walk during the sunrise or evenings with all the...

Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...

Beautiful 'Bay Ridge' has 2,900 square feet of living space and is over 100 years old. With antique furnishings, gorgeous hardwood floors, and luxurious bedrooms, you'll never want to leave this historic vacation rental home for 11 in Annapolis. The 4-bedroom 3.5-bathroom property has a pool house...

All the best of Annapolis awaits at this vacation rental house, set 10 minutes from downtown and only 1 block from Chesapeake Bay! Comfortably hosting 6, this sweet spot offers 3 bedrooms, 2 full baths, 2 half baths, a flagstone patio and screened porch. Watch an Annapolis Boat Show, visit the...

Location: Oceanfront / View: Ocean & Bethany Beach / Sleeps: 8 / 3BR, 2.5BA condo About this home: Just listed for 2019 rentals! Escape to Sea Colony in this upscale eighth floor 3-bedroom, 2.5-bath oceanfront condo! So many great updates (check out the photos to see them all.). Just steps to...

Clear the calendar for an easy-going getaway at this 1-bed, 1.5-bath vacation rental townhouse that sleeps 4 in Annapolis! This house boasts the best of both worlds - a tranquil atmosphere surrounding, and an ideal location just minutes from town. Spend mornings walking the nature trails,...

Annapolis’s historic downtown district is home to museums, marinas, waterfront parks, trendy restaurants, and the US Naval Academy - all of which you’ll find within 1 or 2 miles of this townhome! Boasting 3 bedrooms, 2 bathrooms, a full kitchen, and private patio, this perfectly located vacation...

The lively metropolis of Annapolis awaits at this lovely 4-bedroom, 2.5-bathroom vacation rental condo that sleeps up to 10 guests. While nestled in a quiet neighborhood with lots of yard space, this Annapolis home is only 5 minutes from downtown, 10 minutes from the bay, and within walking...