Description: Stunning 180-degree view of the South River, just off the Chesapeake Bay near Annapolis. The location is incredible. Just 10 minutes to downtown Annapolis and the United States Naval Academy, 40 minutes to Washington, DC, and Baltimore, and 5 minu......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 6

*Rates: extra-night, From: 295  to  295 

*Rates Subject to Change

Description: Private waterfront home in Annapolis, Maryland. Enjoy gorgeous views of the Severn River and Saltworks Creek from our luxurious waterfront home. You can swim and fish from private pier. The large deck is the perfect place to sunbath, or just relax......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 9

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Charming Bay Cottage just steps from a beautiful beach and the Chesapeake Bay, a short drive or walk to the crabbing and fishing pier and easy boat access at Deep Creek. The home is ranch style with hardwood floors and a large back porch, althou......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 6

*Rates: nightly-weekend, From: 250  to  250 

*Rates Subject to Change

Description: Imagine, a little white beach on a quiet peninsula of the Magothy River. Within view of our beach (and deck) are nesting bald eagles, flocks of majestic blue herons and spectacular Chesapeake Bay sunsets! We are located on a unique protected beac......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: weekly, From: 1750  to  1750 

*Rates Subject to Change

Description: Come Join Us In Our Lusiously Appointed Cottage! We are located in the Private Beach Community of Oyster Harbor, Md. Five minutes walk to the beautiful Fishermans Creek and seven minutes walk to our private beach on the Chesapeake Bay. You will......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: extra-night, From: 175  to  175 

*Rates Subject to Change

Description: Large, relaxing contemporary home. Walls of glass and cedar looking out at 3.5 acres of mature woods. The home design is very open and spacious. The modern kitchen is open to the dining room and the sunken living room. Living room has a three-......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 12

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: This is a home away from home with all of the amenities you should expect. The condo is fully furnished with a full and functional kitchen, including stacked washing machine and dryer. The living room has comfy seating for six with a 50' HD plasm......
(Map - Photos - Reviews)

Bedrooms: 1
Sleeps: 2

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Pure Magic! You'll wake to the sound of church bells ringing from St. Mary's, ships horns as they depart from City Dock and horses hooves as they pull carriages through the charming historic streets of Annapolis. This luxuriously decorated histori......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 7

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Be our guest at 19 East Street, in the heart of Historic Annapolis. Walk out the front door, and to your left see the Annapolis State House presiding over the top of the street, turn right and find yourself less than than a block from Gate One o......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 375  to  375 

*Rates Subject to Change

Description: Great getaway for the weekend or the week. Take a leisurely stroll along our community streets and beach or seek the shade of our trails through the woods. Ride a bike or take a run along our quiet, shaded roads and Sandy Points nature trails. Coo......
(Map - Photos - Reviews)

Bedrooms: 1
Sleeps: 3

*Rates: nightly-weekend, From: 175  to  175 

*Rates Subject to Change

Description: This elegant home is the Essence of Annapolis Historic charm! Live like an Annapolitan in this fully furnished charming, beautifully renovated and well maintained detached home on one of the best streets in Historic Annapolis. Comfortably sleeps s......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: This cedar contemporary three-bedroom, two-bath house fronts Almshouse Creek with unobstructed sailboat access to the South River and the Chesapeake Bay, and easy boat access to historic St Michaels on the Eastern Shore. There is a deep-water boat......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 250  to  300 

*Rates Subject to Change

Description: Private waterfront home in Annapolis, Maryland. Enjoy stunning views of the Severn River and Saltworks Creek from practically every room of our charming waterfront cottage. You can swim, fish fand crab from private pier and beach. Pier has three ......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 7

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Wells Cottage: This Magothy River (Mag-oh-thee) family vacation rental was built as a summer cottage by a millionaire in the thirties and retains much of its feel with large wood beam ceilings in the living and dining rooms. Wireless internet is ......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Secluded Waterfront 5 bedroom retreat home on the Magothy River, Annapolis AREA.. Enjoy my wonderful family home only 6 miles from the heart of Annapolis and the Naval Academy. This home is at the end of the roadwhich is on Adams Point ,Shore Acre......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 14

*Rates: nightly-weekend, From: 1200  to  1200 

*Rates Subject to Change

Description: Location, Location, Location! Eastport section of Annapolis, most desirable for ample parking and plethora of best restaurants. End of dead end street w/ views of the Capital dome, St. Mary's churchyard and Carroll House. Walking distance to Hist......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Enjoy the full Ambiance of the Chesapeake ****WE RENT ONLY FOR NAVY COMMISSIONING WEEK***, 2013,& 2014 ARE AVAILABLE ***2012 IS BOOKED This home has been rented to NAVY families for Commissioning week for the past several years. It is considere......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 12

*Rates: weekly, From: 7000  to  7000 

*Rates Subject to Change

Description: A Peaceful Oasis Overlooking Annapolis Waterfront Nestled on two wooded acres of waterfront, this incredible home has 100’ of floor-to-ceiling windows for an expansive view of Weems Creek that’s a perfect secluded getaway for you and your guests.......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 12

*Rates: nightly-weekend, From: 850  to  850 

*Rates Subject to Change

Description: Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views of the Chesapeake Bay Bridge and the ever present sailing regattas taking place just beyond the front yard. Take a leisurely s......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 12

*Rates: extra-night, From: 1000  to  1000 

*Rates Subject to Change

Description: Our waterfront home is located in historic Annapolis two blocks from City Dock and across the street from the Annapolis Yacht Club. There is a view from every room of the harbor and/or Spa Creek, a big beautifully landscaped back yard and eating a......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 10

*Rates: nightly-weekend, From: 1050  to  1050 

*Rates Subject to Change

Description: Great location. in front of the Naval Stadium! Great for after football parties, Commencement week, corporate needs. Available for daily, weekend, weekly or monthly rental. fully furnished, linens, towels, dishes, pots & pans, etc. It is beauti......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 350  to  350 

*Rates Subject to Change

Description: Completely updated Town House, new air conditioning/heating/electric, new kitchen. Enclosed back patio with a new gas grill. Located just 2 1/2 miles from the Navel Academy entrance and down town Annapolis. (One mile and half from the Navy Footbal......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Available for Commissioning Week 2012 and year round rentals. This wonderful 19th century Victorian duplex farmhouse is located near the quiet tip of the Eastport peninsula, only walking minutes away from marinas, sailing schools, restaurants and......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 300  to  300 

*Rates Subject to Change

Description: This charming, immaculate and spacious home on the Eastport Peninsula is directly across from Horn Point Harbor Marina owned by the same family and your stay can be packaged with a slip for up to 110 foot boat. The house is uncluttered and easy to......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 325  to  325 

*Rates Subject to Change

Description: Walk to all your activities! This home is close to all the yacht clubs in Annapolis, restaurants, theatre, shopping, museums, you name it. Naval Academy and St. John's College are a short walk or better yet, take the water taxi to downtown and vis......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 10

*Rates: extra-night, From: 250  to  350 

*Rates Subject to Change

Description: Lovely Contemporary vacation home in ''Arundel On The Bay'' the exclusive community right on the beautiful waters of the Chesapeake Bay. The Historic Highland Beach, fishing pier, Boat launch and community parks all part of the services this wa......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: nightly-weekend, From: 275  to  275 

*Rates Subject to Change

Description: A charming and very spacious Southern Colonial , with large front porch and multiple decks off the back its the perfect setting for family/ friends, also on the days surrounding your wedding day. A perfect home for family reunions/ retreat......
(Map - Photos - Reviews)

Bedrooms: 6
Sleeps: 16

*Rates: nightly-weekend, From: 795  to  795 

*Rates Subject to Change

Description: Sitting on 8 acres of water front property, Our Home on the Cove is a cottage with 5 bedrooms and room for a family of 4 or 15 to run and play. “The Pines” provides space for volleyball, tag, horseshoes and campfires (yum- s’mores), as well as lo......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 15

*Rates: weekly, From: 2850  to  2850 

*Rates Subject to Change

Description: Luxuriously renovated as 4-level loft for residential living in 2003, this 1897 Gothic Revival church retains much of its original architectural character with unparalleled location. At the corner of Maryland Avenue and Prince George Street, you ......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: A perfect home to enjoy your fall football and alumni weekends! Located on King George Street, walking distance to the academy or downtown, this home is open for several fall weekends with a three night minimum. Not a Navy Alum? It is still an ou......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 9

*Rates: nightly-weekend, From: 600  to  850 

*Rates Subject to Change

Description: When you come to Annapolis for a weekend, week or a few months, think about your choices. Stay in one of our fine hotel rooms. You can rent an available owners home and sleep in a room with Timmy's stuffed animals. Or, stay in a home that has just......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 400  to  400 

*Rates Subject to Change

Description: 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. This home offers a 'vacation atmosphere' & acti......
(Map - Photos - Reviews)

Bedrooms: 5
Sleeps: 11

*Rates: weekly, From: 2500  to  2800 

*Rates Subject to Change

Description: No Longer Available for Commissioning Week 2011 and 2012. Featured in the Eastport Home & Garden Tour in 2009. Off street parking plus easy street parking. United States Naval Academy and downtown Annapolis are a short walk, or ride on the water......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 10

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Now Renting for Spring and Summer Weeks of 2011! Our beautiful home was included in Waterfront Living Magazine last summer! Note, we are 18 miles North of Annapolis. We are conveniently located for Annapolis, DC or Baltimore! See link below for ......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 12

*Rates: weekly, From: 2400  to  3800 

*Rates Subject to Change

Description: Waterfront timber frame house in Annapolis, MD. Private, wooded setting with excellent views. This house is an energy efficent 9 year old house perched atop a small bluff overlooking picturesque Mill Creek and an agricultural preserve. The hou......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 6

*Rates: monthly, From: 3900  to  3900 

*Rates Subject to Change

Description: West Annapolis is a village of shops and restaurants in the the quietist part of downtown Annapolis. You can walk to the Naval Academy Stadium and use public transportation to the City Dock or take a relaxing walk through the historic district. It......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 4

*Rates: nightly-weekend, From: 350  to  350 

*Rates Subject to Change

Description: SNUG HARBOR. The perfect place to spend time you visiting your Mid, visit family, tour the City or cheer your sailor or athlete. We have all the amenities you will need for a comfortable visit. Complete kitchen, huge deck with bar-b-cue facili......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 11

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: This new, luxurious Nantucket style home located in Eastport, the heart of Annapolis, is within walking distance of the Sailing Capital of the WORLD! Convenient to shopping and restaurants, with plenty of fun activities you can enjoy your stay wit......
(Map - Photos - Reviews)

Bedrooms: 4
Sleeps: 13

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes fro......
(Map - Photos - Reviews)

Bedrooms: 3
Sleeps: 8

*Rates: extra-night, From: 275  to  350 

*Rates Subject to Change

Description: Perfectly situated this spacious condo has two large bedrooms each with its own bath. Great for couples traveling together or families as the king bed converts to twins and the living room sofa becomes a queen bed. Park you cars in the private lot......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: This wonderful Historic Home is in the perfect location to walk everywhere. You can't beat the location. It's just two houses from City Dock, restaurants, shops, historic sites and three blocks from the Naval Academy! This home was renovated for ......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 5

*Rates: …, From: …  to  … 

*Rates Subject to Change

Description: Booking USNA Football NOW! Oct Boat Shows! Naval Academy Events-reserve early! Fall Games! Parent Weekend! Plebe Weekend. Reunions. Relocation. Family Vacations. Contact for Availability! Best rates possible if you are flexible. We provide r......
(Map - Photos - Reviews)

Bedrooms: 2
Sleeps: 6

*Rates: nightly-weekend, From: 225  to  300 

*Rates Subject to Change