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Annapolis: Vacation Rental By Owner

Search result 1 to 20 Of 138
  • Property-1 Image 1
    House $492 / Nightly
    • 2Bed
    • 3Baths
    • (48) Wonderful
    Annapolis, MD

    When this home was renovated in 2008, no expense was spared to upgrade and decorate this house with every amenity. Cherry hardwood cabinets with stainless... ...more

  • Property-2 Image 1
    Townhome Select Dates for Price
    • 3Bed
    • 3Baths
    Annapolis, MD

    Come stay at this amazing home a mere 100 yds from market square in downtown Annapolis, MD featuring off street parking spots for two mid-size cars or one full... ...more

  • Property-3 Image 1
    Townhome Select Dates for Price
    • 3Bed
    • 6Baths
    • (1) Exceptional
    Annapolis, MD

    Historic Downtown Annapolis Home! Steps from the State House and a block from City Dock in a beautifully renovated home w/ driveway parking on a quiet residential... ...more

  • Property-4 Image 1
    Apartment Select Dates for Price
    • 1Bed
    • 1Baths
    Annapolis, MD

    You will love the convenience of being a short walk/drive to downtown, Rt 50, and the shopping districts from this condominium. Located in a quiet residential... ...more

  • Property-5 Image 1
    House $991 / Nightly
    • 4Bed
    • 3Baths
    Annapolis , MD

    Historic home across from St. John's College, less than a 5 minute walk to the Academy. This four bedroom , two and a half bathroom home has sleeping for eight in... ...more

  • Property-6 Image 1
    House $754 / Nightly
    • 3Bed
    • 3Baths
    • (4) Exceptional
    Annapolis, MD

    3 bedroom/3 bathroom house with bonus room/office with futon. Convenient to downtown (1.5 mile walk), Naval stadium, etc. Sleeps 8 comfortably. First bedroom... ...more

  • Property-7 Image 1
    Villa Select Dates for Price
    • 4Bed
    • 4Baths
    Annapolis, MD

    Property Location When you stay at this villa in Annapolis, you'll be in the suburbs, within a 15-minute drive of Maryland State House and Chesapeake Bay... ...more

  • Property-8 Image 1
    Apartment $195 / Nightly
    • 1Bed
    • 1Baths
    • (46)
    Annapolis, MD

    Completely renovated 1st floor apartment located in the heart of Historic Downtown Annapolis. Everything is within walking distance. Full Kitchen w/ Gas Stove,... ...more

  • Property-9 Image 1
    Townhome Select Dates for Price
    • 4Bed
    • 2Baths
    Annapolis, MD

    Enjoy this beautiful west Annapolis home, complete with spacious living areas, renovated kitchen, in-home gym, and amazing "man cave" with a full bar. Within... ...more

  • Property-10 Image 1
    Cottage $219 / Nightly
    • 1Bed
    • 1Baths
    • (92)
    Annapolis, MD

    Miller Cottage is a charming 1920s style cottage in the quiet neighborhood of Homewood, a quick one mile to Church Circle/West Street and the state capital of... ...more

  • Property-11 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (1) Exceptional
    Annapolis, MD

    A beautiful new 3-level town home in gated community: stainless steel appliances, hardwood floors, indoor/outdoor fireplace on deck, and easy parking. Minutes... ...more

  • Property-12 Image 1
    House $333 / Nightly
    • 2Bed
    • 1Baths
    • (59)
    Annapolis, MD

    A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in this newly-remodeled and totally upgraded... ...more

  • Property-13 Image 1
    House $396 / Nightly
    • 3Bed
    • 2Baths
    • (50)
    Annapolis, MD

    Waterfront timber frame house in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for accurate rates and... ...more

  • Property-14 Image 1
    Guest House Select Dates for Price
    • 1Bed
    • 1Baths
    • (4) Exceptional
    Annapolis, MD

    This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Annapolis and the State house. Easy access /... ...more

  • Property-15 Image 1
    House $948 / Nightly
    • 5Bed
    • 3Baths
    Annapolis, MD

    4 bedrooms plus sofa bed - sleeps 9 in beds (two air mattresses also available to sleep an additional 4). First floor wheelchair accessible bedroom with ADA... ...more

  • Property-16 Image 1
    House $696 / Nightly
    • 4Bed
    • 4Baths
    Annapolis, MD

    Quaint community of Arundel on the Bay in Annapolis, Maryland. Spacious 4 bedroom, 3.5 bathrooms in 3000 s.f. waterfront home on the Chesapeake Bay. with a 30 ft... ...more

  • Property-17 Image 1
    House $1,062 / Nightly
    • 6Bed
    • 5Baths
    Annapolis , MD

    Well-appointed home located five minutes from downtown Annapolis. Walking distance to Supermarket, Pharmacy, banks. Near Chesapeake Bay and Quiet Waters Estuary.... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    • (2) Exceptional
    Annapolis, MD

    3 bedroom 2 bathroom upper level of home directly facing the bay. Full kitchen and screened in porch with hammock. Large yard for games and cooking out. Beach... ...more

  • Property-19 Image 1
    House $1,087 / Nightly
    • 3Bed
    • 4Baths
    Annapolis, MD

    Welcome to our beautiful Annapolis home - perfect for Naval Academy Commissioning Week! This wonderful house is less than a 10 minute walk to the Navy-Marine... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 4Bed
    • 3Baths
    Annapolis, MD

    Walking distance to the Naval Academy - or a quick water taxi ride to the Annapolis dock (steps to the Academy entrance)! Eastport single family home with room... ...more

Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Annapolis. Many accommodations in Annapolis provide "Pets Not Allowed", there are 227, or there are 191 of Vacation Rentals in Annapolis with a "Non Smoking Only", there are also 137 with "Children Welcome", which is another great reason to visit Annapolis.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Annapolis. The most expensive month of the next 12 months is in January, where prices hit an average of $260 a night. In December, prices will hit an average low of $632 per night.