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Annapolis House Rentals

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    Travellers to Annapolis are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    17 Matching Rentals in AnnapolisView all 27 rentals
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    Charming Annapolis home with stunning water views1 / 55
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Charming Home close to historic district1 / 31
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 19, 2017
    This is a great house to rent with another couple or with a family. The house is Within easy walking distance to all the fun in downtown And the waterfront. It has all the...
    Reviewed August 20, 2017
    We had a lovely stay in this spacious and tastefully furnished house. It was perfect for my husband and I and our three boys (8, 14 and 16). The rooms were larger than I...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Excellent Location in Downtown Annapolis- walk to everything !1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Private Garden
    • DVD Player
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 22, 2018
    The house was perfectly located to walk around the downtown area. The house was fully equipped and in great order. Communications with the owner were very good and coordination...
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    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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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We stayed at the cottage for an extended period of time and it was very enjoyable. The house itself was well put together and had everything that we could have needed. The...
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    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
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. We have taken great care and paid pain-staking...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    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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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Grill
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Stunning Home in the Heart of Downtown Annapolis1 / 18
    (1)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 17, 2011
    Our family was gathering for a for a 60th Birthday Celebration and we could not have picked a better location, home, or more accommodating owner. We were trying to find a...
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    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 11
    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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