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Holiday Rentals in Annapolis, MD

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    All 26 Rentals in Annapolis
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    Travellers to Annapolis are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    2 Reviews
    2 BedroomsSleeps 4Quick View
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    3 BedroomsSleeps 7Quick View
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    1 Review
    3 BedroomsSleeps 7Quick View
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    15 Reviews
    3 BedroomsSleeps 6Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Porch
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    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 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...
    Reviewed 8 November 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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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Reviews
    6 BedroomsSleeps 12Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Grill
    • Wi-Fi
    • 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 Reviews
    4 BedroomsSleeps 9Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 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.<BR><BR>We have taken great care and paid pain-staking...
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    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Review
    3 BedroomsSleeps 6Quick 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
    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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    • 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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    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Review
    3 BedroomsSleeps 9Quick 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
    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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    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    2 Reviews
    2 BedroomsSleeps 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
    Reviewed 3 December 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 BedroomsSleeps 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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    Annapolis, Maryland 21146
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    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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    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
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    6 BedroomsSleeps 14Quick View
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    • Washer
    • Waterfront
    • 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- 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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    Annapolis, Maryland 21403
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    3 BedroomsSleeps 8Quick View
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    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
    • Grill
    • Patio
    • 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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    3 BedroomsSleeps 8Quick View
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    • Satellite TV
    • Private Garden
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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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Review
    4 BedroomsSleeps 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
    Reviewed 20 October 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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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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    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 BedroomsSleeps 11Quick View
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    • Waterfront
    • Patio
    • Washer
    • Grill
    • 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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    1 BedroomSleeps 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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    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 BedroomSleeps 2Quick View
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    Pet friendly
    Kid friendly
    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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    5 BedroomsSleeps 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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    3 BedroomsSleeps 6Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Review
    3 BedroomsSleeps 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
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
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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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    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    4 BedroomsSleeps 10Quick View
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    • Ocean Views
    • Waterfront
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    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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    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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