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Annapolis: Vacation Rental By Owner

Search result 1 to 20 Of 30
  • Property-1 Image 1
    Apartment $138 / Nightly
    • 2Bed
    • 1Baths
    This 2nd Floor Apartment, with its... Annapolis, MD

    This 2nd floor privately owned apartment has its own off street parking, sidewalk and entrance. It is clean as a whistle and neat as a pin. The private... ...more

  • Property-2 Image 1
    House $438 / Nightly
    • 4Bed
    • 4Baths
    Don't miss out on this - Great price... Annapolis, MD

    6 miles from USNA. Max. # of People Permitted: 07-10. This comfortable family home has 4 bedrooms with three baths. Home has a queen, 2 doubles and 2 twins.... ...more

  • Property-3 Image 1
    Villa Select Dates for Price
    • 4Bed
    • 4Baths
    Annapolis home with many amenities 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-4 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    Comfortable Single Family Home 3... Annapolis, MD

    Comfortable single family home with private brick patio and BBQ grill as well as large back yard, playground set and driveway parking for 3 cars. First floor... ...more

  • Property-5 Image 1
    House $905 / Nightly
    • 4Bed
    • 4Baths
    Attractive expanded cape on St.... Annapolis, MD

    Private Pool. 4 miles from USNA. Sleeps 12. Attractive expanded cape on St. Margarets Road has a large yard with a pool that may or may not be open by... ...more

  • Property-6 Image 1
    House $704 / Nightly
    • 5Bed
    • 3Baths
    5-BR/3Ba home. 51" plasma TV with... Annapolis, MD

    If it rains all through Commissioning Week you'll still be happy in this 5-BR/3Ba home. 51" plasma TV with Bose Surround-Sound, pool table, and exercise... ...more

  • Property-7 Image 1
    House $342 / Nightly
    • 3Bed
    • 2Baths
    • (50)
    Comfortable Timber Frame deep... 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-8 Image 1
    Apartment Select Dates for Price
    • 1Bed
    • 1Baths
    This spacious and well constructed... Annapolis, MD

    This spacious and well constructed in-law apartment has a 1 car garage. Entire lower level of private home with lovely patio outdoors and a wood burning stove... ...more

  • Property-9 Image 1
    Room $59 / Nightly
    • 1Bed
    • 1Baths
    • (2) Exceptional
    C/ean & Cozy Annapolis, Maryland

    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... ...more

  • Property-10 Image 1
    House $89 / Nightly
    • 1Bed
    • 2Baths
    Annapolis Townhome w/Deck by Nature... Annapolis, Maryland

    Clear the calendar for an easy-going getaway at this 1-bed, 1.5-bath vacation rental townhouse that sleeps 4 in Annapolis! This house boasts the best of both... ...more

  • Property-11 Image 1
    House $1,050 / Nightly
    • 4Bed
    • 4Baths
    Resort like living five miles from... Annapolis, MD

    You and your family will love this single family two-story colonial to celebrate an Academy celebration. After many years of sponsorship, our Mids and their... ...more

  • Property-12 Image 1
    Townhome $391 / Nightly
    • 3Bed
    • 3Baths
    Woods Landing is conveniently located... Annapolis, MD

    6 miles from USNA. Max. # of People Permitted: 08. This attractive 3 BR/ 2.5 BA townhouse can sleep 8+ in a king, a double, a queen and a double sleep sofa, and... ...more

  • Property-13 Image 1
    Townhome Select Dates for Price
    • 1Bed
    • 2Baths
    • (6) Excellent
    Annapolis Townhome w/Deck by Nature... Annapolis, MD

    Clear the calendar for an easy-going getaway at this 1-bed, 1.5-bath vacation rental townhouse that sleeps 4 in Annapolis! This house boasts the best of both... ...more

  • Property-14 Image 1
    House $383 / Nightly
    • 4Bed
    • 3Baths
    Fully Furnished 4 Bedroom/3 Bathroom... Annapolis, MD

    2 month minimum stay. $4300/mo. Pets considered. This fully furnished home is located in Pendennis Mount and part of the Broadneck School District. 4... ...more

  • Property-15 Image 1
    House $300 / Nightly
    • 4Bed
    • 3Baths
    • (8) Wonderful
    Lovely family home just minutes from... Annapolis, MD

    Welcome to the Cape! We offer our recently upgraded home in the Cape St Claire neighborhood of Annapolis. Just minutes from downtown Annapolis we have off street... ...more

  • Property-16 Image 1
    House Select Dates for Price
    • 6Bed
    • 7Baths
    Cedar Lane Farm Chateau - Your Own... Annapolis, MD

    1524 YOUR OWN PRIVATE COUNTRY CLUB Incomparable Continental Waterfront Estate in Annapolis, Maryland's historic state capital! Panoramic Whitehall Creek VIEWS... ...more

  • Property-17 Image 1
    House $1,277 / Nightly
    • 6Bed
    • 7Baths
    Beautiful 6 bedroom home in St.... Annapolis, MD

    Check out this beautiful 6 bedroom home in St. Margaret's, just 3.2 miles from the Naval Academy, less than a 10 minute drive. Both the kids and adults will love... ...more

  • Property-18 Image 1
    House Select Dates for Price
    • 4Bed
    • 4Baths
    PRIVATE BEACH & magnificent views of... Annapolis, MD

    Lovely & Spacious Severn River Waterfront - Beautifully furnished and fully equipped 4BR/4FB home with private beach & magnificent views of the Severn River.... ...more

  • Property-19 Image 1
    House Select Dates for Price
    • 4Bed
    • 2Baths
    NEW! Annapolis Home w/ Deck &... Annapolis, MD

    Experience the East Coast like never before at this charming 4-bedroom, 2-bathroom vacation rental house in Annapolis! With enough space to sleep 8, this... ...more

  • Property-20 Image 1
    House Select Dates for Price
    • 4Bed
    • 5Baths
    Perfect for your short or long term... Annapolis, MD

    Are you relocating your family or getting renovations done to your home? This house is perfect for your short or long term stay! With 4 floors of livings and 4... ...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 December, prices will hit an average low of $498 per night.