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North Beach Vacation Rentals

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    All 51 Rentals in North Beach
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    Don't let other travelers get your favorite North Beach area vacation rental. You're so close to securing your perfect getaway. Book today.
    North Beach
    4.5 of 5 bubbles
    5 Reviews
    1 Bedroom, Sleeps 5Quick View
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    North Beach
    3 Bedrooms, Sleeps 6Quick View
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    North Beach
    4 Bedrooms, Sleeps 10Quick View
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    North Beach
    2 Bedrooms, Sleeps 4Quick View
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    North Beach, Calvert County 20714
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Beach
    2 Bedrooms, Sleeps 6Quick View
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    • DVD Player
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    Pet friendly
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    North Beach, Calvert County 20714
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    North Beach
    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    All-Decked-Out Beach House is on the Western Shore of the Chesapeake Bay in the lovely Rose Haven/North Beach MD community. Fenced-in on a large corner lot directly across from Herrington on the Bay, 3 miles from Chesapeake Beach Bay Resort & Spa and 45 min. from DC this 3bed/1.5 bath offers...
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    North Beach, Calvert County 20714
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Beach
    3 Bedrooms, Sleeps 6Quick View
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    North Beach, Calvert County 20714
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    North Beach
    3 Bedrooms, Sleeps 8Quick View
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    Pet friendly
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    North Beach, Calvert County 20714
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Beach
    2 Bedrooms, Sleeps 4Quick View
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    North Beach, Calvert County 20714
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 20 miles of North Beach.
    Annapolis, MD
    5 of 5 bubbles
    15 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed December 11, 2016
    We absolutely loved our time in this home! We were in town for the Annapolis Half Marathon. We walked to the starting line from the house, and even walked downtown and the...
    Excellent of 5 bubbles
    Reviewed November 8, 2016
    This quaint home has loads of charm and plenty of space. Convenient to all the locations that were important to us, we walked to the Navy-Marine Corp Memorial Stadium and only...
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    About this property
    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. <BR>Sun Porch & Plenty of parking.<BR>A perfect place to relax and enjoy Annapolis, the property is available all year...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Washer
    • Terrace
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    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed June 29, 2014
    We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
    Excellent of 5 bubbles
    Reviewed November 12, 2013
    My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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    About this property
    Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has queen size bed. Large loft has two single beds. Although the condo can accommodate 6 for sleeping, I will generally only rent to parties of 4 or fewer. Dining room can seat 8 +...
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Annapolis, MD
    3 Bedrooms, Sleeps 7Quick View
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    • Private Yard
    • DVD Player
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Annapolis, MD
    4.5 of 5 bubbles
    3 Reviews
    4 Bedrooms, Sleeps 9Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed June 21, 2015
    Owner has everything imaginable in the home that you would ever need for a vacation getaway. The house has lots of room so you have your privacy when needed. Beautiful...
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    About this property
    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.<BR><BR>We have taken great care and paid pain-staking...
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    Annapolis, MD
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
    • Grill
    • DVD Player
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    • Patio
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Edgewater, MD
    3 Bedrooms, Sleeps 12Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2000 square foot apartment is in a beautiful, gated resort marina. The apartment is completely new with high end kitchen and bathrooms, cathedral ceilings and an amazing view all the way down the South River. The marina offers all kinds of activities including a waterfront restaurant, Jet...
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    Location Information
    Edgewater, Maryland 21037
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Annapolis, MD
    4 Bedrooms, Sleeps 10Quick View
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    • Grill
    • Patio
    • Terrace
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Annapolis, MD
    5 Bedrooms, Sleeps 11Quick View
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    • Waterfront
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21032
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Annapolis, MD
    3 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
    • Private Yard
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Deale, MD
    2 Bedrooms, Sleeps 6Quick View
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    • Satellite TV
    • Housekeeping Included
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the home and studio of local sculptor artist. This apartment includes the second and third floors, approximately 2,300 sf of space. Large and comfortable bedrooms, large bathrooms, showers have double heads, sauna in the main master-bath. We provide linens and towels. This apartment has a...
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    Location Information
    Deale, Maryland 20751
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Annapolis, MD
    5 Bedrooms, Sleeps 20Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    Tilghman, MD
    5 of 5 bubbles
    6 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • Washer
    • DVD Player
    • Satellite TV
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    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed July 21, 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    Excellent of 5 bubbles
    Reviewed October 8, 2015
    Tilghman Cottage (the Roost) is a lovely place that makes you feel comfortable in every possible way. The house is very clean, bright, cosy, and yet spacious, fully equipped...
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    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina...
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    Location Information
    Tilghman, Talbot County 21671
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Neavitt, MD
    3 Bedrooms, Sleeps 9Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated cottage in the village of Neavitt. Neavitt is a great village only 10 minutes away from St. Michaels. The house has waterviews and access to it's own personal dock which is great for fishing, kayaking or paddle boarding. Spend the day out on local waterways and then relax the night...
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    Neavitt, Talbot County 21652
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Neavitt, MD
    2 Bedrooms, Sleeps 5Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring...
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    Location Information
    Neavitt, Talbot County 21652
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Annapolis, MD
    3 Bedrooms, Sleeps 8Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Central Heating
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Annapolis, MD
    2 Bedrooms, Sleeps 5Quick View
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    • Washer
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Annapolis, MD
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 7Quick View
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    • Grill
    • Terrace
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed November 16, 2016
    Beautifully decorated. Walking distance to Naval Academy. Plenty of sleeping space. Private outdoor space.
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    About this property
    Walk to the city docks and naval academy in this new (2014) luxury townhouse. The king bedroom suite also has a pullout twin bed for parents with small children. Enjoy the grand piano or relax by the gas fireplace. Cookout on the sunny patio. Visit local pubs and restaurants or just walk to...
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    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    McDaniel, MD
    5 Bedrooms, Sleeps 10Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock...
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    Location Information
    McDaniel, St. Michaels 21647
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Annapolis, MD
    6 Bedrooms, Sleeps 14Quick View
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    • Washer
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding- With its magazine worthy gardens, and spacious 6 bedrooms, designed and furnished with the highest level of comfort, and relaxation. For over 9 years now we have been...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Annapolis, MD
    3 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 9Quick View
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    • DVD Player
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    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Average of 5 bubbles
    Reviewed September 27, 2016
    Location quiet with good views.Disappointed that house was advertised with hot tub which was one of the main reasons this home was selected, and there was no hot tub. Owner...
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    About this property
    Come stay in this beautiful 3-bedroom, 3.5-bathroom single-family home on Oyster Creek – You’ll be able to enjoy fantastic views of the Chesapeake Bay from almost every single room! There’s enough room for 9 guests to comfortably sleep here, so it’s a great size for a family retreat. The...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Annapolis, MD
    1 Bedroom, Sleeps 2Quick View
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    Pet friendly
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    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Saint Leonard
    2 Bedrooms, Sleeps 6Quick View
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    • Grill
    • Waterfront
    • Internet Access
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    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
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    Location Information
    Saint Leonard, Calvert County 20685
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    3 Bedrooms, Sleeps 6Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
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    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HOUSE<BR>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...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Upper Marlboro, MD
    1 Bedroom, Sleeps 2Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clean, comfortable private rooms and baths in quiet Pet Friendly (P/F) Cul de Sac. Located in an established golf community. Great location. Only 15 miles from DC capitol and 1 hr from Baltimore harbor. 40 mins from casinos. Large home with owners on premises.Backs up to a nature reserve with...
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    Location Information
    Upper Marlboro, Maryland 20772
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Shady Side, MD
    2 Bedrooms, Sleeps 5Quick View
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    • Air Conditioning
    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If mesmerizing waterfront views, tidy and comfortable accommodations, and a private backyard are what you are longing for, then escape to this 2-bedroom, 1.5-bathroom vacation rental house in Shady Side, Maryland! With access to a private pier and dock, this quaint cottage that comfortably sleeps 5...
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    Location Information
    Shady Side, Maryland 20764
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Annapolis, MD
    5 of 5 bubbles
    3 Reviews
    6 Bedrooms, Sleeps 12Quick View
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    • DVD Player
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    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed October 21, 2015
    Our group of 6 couples rented this lovely home during the Annapolis, MD Annual Powerboat Show. Having stayed in hotels for prior boat shows, we wanted to have the freedom and...
    Excellent of 5 bubbles
    Reviewed September 27, 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
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    About this property
    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...
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    Location Information
    Annapolis, Maryland 21405
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    Annapolis, MD
    2 Bedrooms, Sleeps 5Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is good for couples, solo adventurers, and business (URL HIDDEN) school just down the street , Great location for naval academy parents for parents day etc. A gourmet kitchen if you prefer to cook your own meals or cook your fish you have caught on your fishing trip on the bay,we can...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Annapolis, MD
    1 Bedroom, Sleeps 2Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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....
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    Location Information
    Annapolis, Maryland 21409
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Annapolis, MD
    4 Bedrooms, Sleeps 10Quick View
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    • Patio
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Property (built in 2000) minutes outside Annapolis, Maryland. Expansive views of the river from this gated custom built home (2176 sq ft excluding basement) with 278' pier on private lot with your own 50' sandy beach. This comfortable home boasts 3-4 bedrooms (and Murphy bed in the...
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    Location Information
    Annapolis, Maryland 21146
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Clinton, MD
    4 Bedrooms, Sleeps 14Quick View
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    • Washer
    • Grill
    • Balcony
    • Housekeeping Included
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sits on a gated 7.5 acres flat land. Makes you feel living in the country and yet so close to the city. Easy 30 minutes drive or less to Washington DC, National Harbor, MGM Casino, Tanger outlets, Old Town Alexandria, Andrews/Bolling Airforce bases, and many more. Adjacent to the property was a...
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    Location Information
    Clinton, Maryland 20735
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Wittman, MD
    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. Upstairs features two sleeping areas - a bedroom with two extra long twin beds that can be combined to make a king and an open, loft-style bedroom with a queen bed and...
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    Location Information
    Wittman, Talbot County 21676
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis, MD
    5 of 5 bubbles
    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • Porch
    • Internet Access
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed December 3, 2016
    My two friends and I wanted a place to get away close to our homes in PA and we found it. Annapolis provided everything we were looking for and the house was beautiful and...
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    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Annapolis, MD
    4 Bedrooms, Sleeps 10Quick View
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    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROTECTED WATERS, GREAT ANCHORAGES... …gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing destination on the East...
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Saint Leonard
    2 Bedrooms, Sleeps 4Quick View
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    • Parking
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The "Sweet Spot" on the Bay - this charming 2 BR 1 Bath Cottage with water views is located in a private waterfront community, Long Beach in St. Leonard, MD, just half a block to the beach (which has a nice big shade tree). This cozy little cottage is super comfy and fully furnished with linens...
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    Location Information
    Saint Leonard, Calvert County 20685
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Annapolis, MD
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the United States has a little something for every interest and taste, whether you're a history buff, a sports enthusiast, or someone simply looking for a peaceful retreat!   Have the...
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    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bozman, MD
    5 of 5 bubbles
    10 Reviews
    8 Bedrooms, Sleeps 27Quick View
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    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed November 14, 2016
    We thoroughly enjoyed our stay in one of the little cottages on the property. We arrived late Friday night and the property sign was not lit up, so it took a while to find it...
    Excellent of 5 bubbles
    Reviewed June 9, 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is...
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
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    Location Information
    Bozman, Talbot County 21612
    Rental Home - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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    Saint Leonard
    1 Bedroom, Sleeps 2Quick View
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    • Waterfront
    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from...
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    Location Information
    Saint Leonard, Calvert County 20685
    Rental Home - 1 Bedroom, Sleeps 2
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    Annapolis, MD
    3 Bedrooms, Sleeps 9Quick View
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    • Grill
    • Satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect home to enjoy time in Annapolis!  Located on King George Street, walking distance to the Academy or downtown, this home is open year round with a 2-night minimum stay. It is an outstanding home for Weddings, Academy Events, Alumni Gatherings or Family Vacations.  This stunningly...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Claiborne, MD
    5 of 5 bubbles
    5 Reviews
    3 Bedrooms, Sleeps 8Quick View
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    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed June 27, 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    Excellent of 5 bubbles
    Reviewed October 10, 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake...
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    Location Information
    Claiborne, Talbot County 21663
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Annapolis, MD
    4 of 5 bubbles
    1 Review
    4 Bedrooms, Sleeps 14Quick View
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    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed October 20, 2015
    Myself and five coworkers rented this house for a meeting. As we are from different areas across the country we usually meet at hotels. I thought we would try something...
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    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home & property. Cut and paste the following link: AnnapolisWaterfrontRentals..om This incredible home has 100' of floor-to-ceiling windows nestled in the tree canopy for...
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Annapolis, MD
    5 of 5 bubbles
    1 Review
    3 Bedrooms, Sleeps 6Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 1 week ago
    A clean, peaceful retreat with spectacular views; that is exceptionally stocked! I had no need to buy anything! At one point, I asked the owner if/or where the hand mixer...
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    About this property
    Waterfront timber frame large cottage in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for rates and quote. This house is an energy efficient 9 year old house perched atop a small bluff overlooking picturesque Mill Creek and an...
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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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