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Annapolis House Rentals

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    Travellers to Annapolis are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in AnnapolisView all 22 rentals
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    Charming and Spacious Annapolis Victorian1 / 19
    (5)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 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
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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 20 October 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 21 August 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
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • 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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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    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-76 five Star reviews can be viewed on our sister site-vacation rentals by owner dot com. 230476 With its magazine worthy gardens, and spacious 6 bedrooms, designed and...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    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
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    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
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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 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
    The ultimate Maryland retreat awaits you when you stay at this beautiful 3-bedroom, 3.5-bathroom vacation rental home on Oyster Creek. Up to 9 lucky guests will enjoy incredible views of the Chesapeake Bay and unbeatable maritime location close to the beach, boating, and fresh seafood. Whether you...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    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
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Terrace
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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