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Annapolis Holiday Rentals

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    Travellers to Annapolis are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Annapolis
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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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    Beautiful Eastport Home, Walk to Naval Academy1 / 15
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Charming Home close to historic district1 / 29
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Charming and Spacious Annapolis Victorian1 / 24
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Air Conditioning
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    • Grill
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    • Washer
    • Porch
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 October 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...
    Reviewed 27 September 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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    Annapolis, Maryland 21405
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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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 27 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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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Annapolis Waterfront very near USNA1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    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 was...
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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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    Annapolis, Maryland 21409
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Beach Cottage: Newly Remodeled and Family Friendly!1 / 22
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Refinished W/Best Backyard In Annapolis, Minutes From Downtown & Naval Academy1 / 24
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick 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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    Annapolis, Maryland 21032
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    Suitability
    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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    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (17)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2017
    My family just moved here in December 2016 and we needed a place to stay for a new months. It turned into 6 months and Alka B. was a wonderful landlord and was very helpful with...
    Reviewed 13 July 2017
    The location is amazing, especially for Navy football games! Plus the owner is right next door and very responsive for any questions or needs. Very accommodating and helpful...
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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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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ideal for Family Get Togethers, Stadium Events, Academy Events & More1 / 17
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Internet Access
    • Washer
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    • Satellite TV
    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedroom, 3.5 Bath, Located Near Downtown Annapolis1 / 14
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Home ideal for USNA Induction Day, Plebe Parents Weekend, and Class Reunions1 / 24
    (1)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
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    • Washer
    • 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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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
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    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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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Internet Access
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Studio, 2 Bathrooms, Sleeps 18 Quick View
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    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 2 Bathrooms, Sleeps 18
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Waterfront
    • Satellite TV
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    • Air Conditioning
    • DVD Player
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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-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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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 50
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    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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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Enjoy your time spent in Annapolis!1 / 22
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Beautiful Annapolis Getaway- Walk Everywhere!!!1 / 19
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful family-friendly 4-Bdr home in Murray Hill1 / 22
    (3)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Stunning home in the Historic District1 / 24
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    Gorgeous Luxury Home steps to USNA/State House/City Dock-CHRISTMAS Avail bc cxl1 / 14
    (7)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lovely Eastport Artists Home/ Near Naval Academy, Marinas and Yacht Clubs1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Large Contemporary in Wooded Privacy1 / 20
    (5)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
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    Annapolis, Maryland 21401
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Summer in Murray Hill/Rent a Paddle board or Kayak on Spa Creek 2 blocks away!1 / 22
    (10)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Balcony
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    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Clean & Spacious Reserve Home or Individual room1 / 16
    (4)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
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    Annapolis, Maryland 21409
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Visit Downtown Historic Annapolis And The Naval Academy1 / 21
    (19)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Heart of the Historic District!1 / 18
    (20)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Historic Downtown Annapolis Home for Rent- Steps to Naval Academy1 / 17
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Annapolis Area Home With Pool! Minutes To Downtown1 / 23
    (3)Average
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Quiet Relaxing Waterfront Swiss Chalet- Fall/Winter Weekly and Monthly Specials!1 / 24
    (9)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Annapolis, Maryland 21409
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Charming Historic Annapolis Home - Superior Downtown Location!!!1 / 24
    (25)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • Terrace
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly renovated Eastport Annapolis house with water views1 / 16
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA1 / 24
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21409
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic Annapolis Home And Garden1 / 23
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Large and Luxurious! Perfect For Chesapeake Bay Foundation Wedding Groups!1 / 24
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    Annapolis Condominium in the Heart of Historic Downtown1 / 24
    (38)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Perfect Location For Naval Academy Events & Boat Shows1 / 16
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Steps Away from Historic Downtown / Close to USNA1 / 18
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Discounted rates,  Across from Gate 1 USNA, 1 block to the Downtown harbor1 / 23
    (24)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Historic District - 1 Block to Naval Academy & State House1 / 9
    (20)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Historic District Home with Gorgeous Renovation1 / 24
    (11)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Annapolis Historic District Apartment1 / 19
    (10)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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