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Annapolis: Vacation Rental By Owner

Search result 1 to 20 Of 97
  • Property-1 Image 1
    Apartment Select Dates for Price
    • 3Bed
    • 2Baths
    Annapolis, Maryland

    The PupPad is an amazing space with even better views. Listen to the soft clank of the sailboat masts in the breeze and watch the sunlight dance on the water. We... ...more

  • Property-2 Image 1
    Villa $695 / Nightly
    • 5Bed
    • 3Baths
    Annapolis, Maryland

    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached... ...more

  • Property-3 Image 1
    House $300 / Nightly
    • 3Bed
    • 4Baths
    Annapolis, Maryland

    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office +... ...more

  • Property-4 Image 1
    House Select Dates for Price
    • 4Bed
    • 4Baths
    Annapolis, Maryland

    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... ...more

  • Property-5 Image 1
    House Select Dates for Price
    • 3Bed
    • 1Baths
    • (2) Exceptional
    Annapolis, Maryland

    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,... ...more

  • Property-6 Image 1
    House $715 / Nightly
    • 5Bed
    • 3Baths
    Annapolis, Maryland

    Beautiful 'Bay Ridge' has 2,900 square feet of living space and is over 100 years old. With antique furnishings, gorgeous hardwood floors, and luxurious bedrooms,... ...more

  • Property-7 Image 1
    House $449 / Nightly
    • 3Bed
    • 4Baths
    Annapolis, Maryland

    All the best of Annapolis awaits at this vacation rental house, set 10 minutes from downtown and only 1 block from Chesapeake Bay! Comfortably hosting 6, this... ...more

  • Property-8 Image 1
    House Select Dates for Price
    • 3Bed
    • 2Baths
    Annapolis, Maryland

    This beautiful 3br home on the peninsula in Eastport is perfect for your Annapolis visit. It is within walking distance to popular attractions including local and... ...more

  • Property-9 Image 1
    Apartment $250 / Nightly
    • 2Bed
    • 1Baths
    Annapolis, Maryland

    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... ...more

  • Property-10 Image 1
    House $375 / Nightly
    • 3Bed
    • 4Baths
    Annapolis, Maryland

    HOUSEBRThis fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three... ...more

  • Property-11 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 1Baths
    Annapolis, MD

    3 month minimum. $3600/mo. On the warm evenings of summer grab your beverage of choice and meander down to pool side to get to know the wonderful neighbors of... ...more

  • Property-12 Image 1
    House $448 / 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 $1,057 / Nightly
    • 5Bed
    • 4Baths
    Annapolis, MD

    Behold your perfect Annapolis getaway home! This gorgeous 5 bedroom, 3.5 bathroom home has breathtaking views of the Chesapeake Bay in the Bay Ridge Community. A... ...more

  • Property-14 Image 1
    Condo Select Dates for Price
    • 2Bed
    • 2Baths
    Annapolis, MD

    An Annapolis dream unit! This great garden-style condo is located in the gated Shearwater Community in Eastport with a fabulous deck overlooking Spa Creek. It is... ...more

  • Property-15 Image 1
    Studio Select Dates for Price
    • 1Bed
    • 1Baths
    Annapolis, MD

    This wonderful efficiency unit is in a secured building with convenient access to everything in Eastport and downtown. The unit offers an open floor plan, a new... ...more

  • Property-16 Image 1
    House $626 / Nightly
    • 5Bed
    • 4Baths
    Annapolis, MD

    Beautiful, recently updated 5 bedroom/3.5 bathroom single family home located in Annapolis Cove just 4.3 miles from the Naval Academy. Finished basement with... ...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 $610 / 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-19 Image 1
    Condo Select Dates for Price
    • 1Bed
    • 1Baths
    Annapolis, MD

    6 month minimum. $2600/mo. Enjoy this wonderful condo in the heart of Eastport, Annapolis, Maryland. Walk to pubs, restaurants, and wine bars. Condo has new... ...more

  • Property-20 Image 1
    Apartment $157 / Nightly
    • 1Bed
    • 1Baths
    Annapolis, MD

    This quaint little cottage is the perfect getaway retreat for a week. It has just what you need to stay there and enjoy your time in Annapolis. This unit is in... ...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 $271 a night. In February, prices will hit an average low of $0 per night.