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Shady Side Vacation Rentals

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    All 21 Rentals in Shady Side
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    The following rentals are within 10 miles of Shady Side.
    Charming and Spacious Annapolis Victorian1 / 19
    (6)Excellent
    Annapolis
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (19)Excellent
    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Annapolis
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • 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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    Annapolis, Maryland 21032
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    Seahorse Guest Cottage near the Bay, dog friendly1 / 17
    (5)Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 15, 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    Reviewed July 8, 2013
    We absolutely fell in love with this quiet little cabin a block away from Chesapeake Bay. Gary, the owner, met us at the cabin and personally gave us a tour of the cabin and let...
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    About this property
    The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full...
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    Location Information
    North Beach, Calvert County 20714
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    Annapolis
    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All-Decked-Out Beach House is on the Western Shore of the Chesapeake Bay in the lovely Rose Haven/North Beach MD community. Fenced-in on a large corner lot directly across from Herrington on the Bay, 3 miles from Chesapeake Beach Bay Resort & Spa and 45 min. from DC this 3bed/1.5 bath offers...
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    North Beach, Calvert County 20714
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 51
    (2)Excellent
    Annapolis
    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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Annapolis
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • 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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to...
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    Location Information
    North Beach, Calvert County 20714
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    Annapolis
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Annapolis
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 20
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    Annapolis
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Cable/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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    C/ean & Cozy1 / 10
    (2)Excellent
    Annapolis
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 5, 2018
    Accommodating hostess. Thank you for your hospitality. The room was neat and clean. Close to inner city, Annapolis.
    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
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick 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 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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    Annapolis
    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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Charming Home close to historic district1 / 31
    (4)Excellent
    Annapolis
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Annapolis
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Yard
    • 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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Annapolis
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Annapolis
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxury Boat & Bed 78' Motor Yacht 'Laid Off'1 / 18
    (1)Excellent
    Edgewater
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We stayed aboard the Laid Off for a friends 40th birthday celebration and had a wonderful evening watching the sunset surrounded by friends and family! It was a relaxing evening...
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    About this property
    Our luxury 78' Hatteras Motor Yacht, 'Laid Off' is an exciting experience to stay on for the day, overnight, weekend or a week. The Yacht offers 4 luxury staterooms each with its own bathroom. The large living room has a piano, lounge seating, flat screen TV/entertainment center with karaoke....
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    Location Information
    Edgewater, Maryland 21037
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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