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Annapolis Vacation Rentals

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    Travelers to Annapolis are booking September dates now. Secure your vacation rental today, and have the perfect trip.
    All 95 Rentals in Annapolis
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    Charming and Spacious Annapolis Victorian1 / 48
    (3)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Beautiful Eastport Home, Walk to Naval Academy1 / 30
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 50
    (17)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beautiful Murray Hill Home (Annapolis)1 / 60
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
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    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.<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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    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Patio
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    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    Charming Home close to historic district1 / 29
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Grill
    • Porch
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    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...
    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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    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bdrm Apt DTA - Great Location!!1 / 18
    (16)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Annapolis, Maryland 21401
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Waterfront
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    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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    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
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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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    Spacious, Modern Condo nr. Navy Stadium, downtown & Mall . Easy access route 501 / 6
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Terrace
    • Satellite TV
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    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    C/ean & Cozy1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
    Reviewed June 19, 2017
    Very nice, clean, comfortable. Hostess was very accomodating. Would plan on staying there again if another trip to the area is warranted
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    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 Waterfront very near USNA1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Air Conditioning
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 15, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 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 21401
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Yard
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    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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    Quiet Relaxing Waterfront Swiss Chalet, Fall and Winter rates available!1 / 24
    (8)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 50
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    • Housekeeping Included
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    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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    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
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    • DVD Player
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    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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    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Grill
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Private Newly Finished Basement Apartment, 1 Mile Walk To Downtown Annapolis.1 / 12
    (11)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
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    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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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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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
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    • Secure Parking
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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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    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    • Satellite TV
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gorgeous Luxury Home steps to USNA/State House/City Dock-CHRISTMAS Avail bc cxl1 / 14
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Amazing Waterfront Annapolis & easy walk downtown1 / 24
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Less Than A Block From Main Street - Heart Of Historic District!1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Historic District Home with Gorgeous Renovation1 / 24
    (9)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Location Information
    Annapolis, Maryland 21409
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEAUTIFUL 6500 Sq ft, 3 MILES USNA, Annapolis.  Close to Washington DC.1 / 22
    (4)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 18 Quick View
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    Annapolis, Maryland 21401
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 18
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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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    • Grill
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    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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    LUXURY DOWNTOWN HOME - WALK TO EVERYTHING ANNAPOLIS HAS TO OFFER!1 / 24
    (54)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Balcony
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    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    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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    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Heart of Downtown, superior location!1 / 17
    (7)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Patio
    • Grill
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Large Luxury Apartment In Downtown Annapolis1 / 11
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cozy Beach Cottage: Newly Remodeled and Family Friendly!1 / 22
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Air Conditioning
    • Satellite TV
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
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    • Balcony
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    • Porch
    • Wi-Fi
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    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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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    • Hot Tub
    • Grill
    • Satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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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
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Satellite TV
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    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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    4 Bedroom, 3.5 Bath, Located Near Downtown Annapolis1 / 14
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Satellite TV
    • Parking
    • Patio
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21403
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    • Grill
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Patio
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Annapolis, Maryland 21401
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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