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Annapolis: Vacation Rental By Owner

Search result 1 to 20 Of 137
  • Property-1 Image 1
    Townhome Select Dates for Price
    • 3Bed
    • 6Baths
    • (1) Exceptional
    Steps from the State House and a... 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-2 Image 1
    Townhome $383 / Nightly
    • 3Bed
    • 2Baths
    DOWNTOWN ANNAPOLIS DREAMHOME... Annapolis, MD

    Your Downtown Annapolis dream home awaits! This elegant brick home sits in the heart of Annapolis within walking distance to all major points of interest.... ...more

  • Property-3 Image 1
    House $948 / Nightly
    • 5Bed
    • 3Baths
    Clean, Spacious Family House... 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-4 Image 1
    Townhome Select Dates for Price
    • 3Bed
    • 3Baths
    Amazing home a mere 100 yds from... 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-5 Image 1
    House $777 / Nightly
    • 4Bed
    • 4Baths
    Take a look at this Murray Hill Gem!... Annapolis, MD

    Take a look at this Murray Hill Gem! Enjoy your next Annapolis stay in the wonderful home built in 1931. Inside this Historic home is a beautiful and modern... ...more

  • Property-6 Image 1
    Townhome $602 / Nightly
    • 3Bed
    • 4Baths
    • (1) Very Good
    Downtown Historic District Annapolis... Annapolis, MD

    Downtown Annapolis Townhome with Attached Garage Parking! Lovely newer upscale residence built in 2008 located in one of the most sought-after areas in... ...more

  • Property-7 Image 1
    House $923 / Nightly
    • 3Bed
    • 3Baths
    • (4) Exceptional
    3 bedroom house near Navy Stadium 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-8 Image 1
    Apartment Select Dates for Price
    • 1Bed
    • 1Baths
    One-bedroom apartment with fireplaces... Annapolis, MD

    One-bedroom apartment with fireplaces in all three rooms: living room, kitchen and bedroom. Cozy front porch. 5 minute walking distance to City Dock. Rate is... ...more

  • Property-9 Image 1
    House Select Dates for Price
    • 4Bed
    • 3Baths
    Water view from every window -... Annapolis, MD

    This home is the jewel in the crown of Epping Forest. Located at the point where the deep water of Saltworks Creek meets the Severn River with water views from... ...more

  • Property-10 Image 1
    Townhome Select Dates for Price
    • 4Bed
    • 2Baths
    RENOVATED kitchen, in-home gym, and... 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-11 Image 1
    Apartment Select Dates for Price
    • 1Bed
    • 1Baths
    You will love the convenience of... 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-12 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (1) Exceptional
    Modern Comfort in Great Location 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-13 Image 1
    Townhome Select Dates for Price
    • 3Bed
    • 3Baths
    Charming row house in the Heart of... Annapolis, MD

    3 Bedroom Historic Downtown Annapolis Vacation Rental: Charming row house in the Heart of the Historical District, within 2 blocks to the City Dock. This home has... ...more

  • Property-14 Image 1
    House $626 / Nightly
    • 3Bed
    • 2Baths
    One block from USNA Gate 1, or 3... Annapolis, MD

    One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe! Nicely furnished, with a large collection of... ...more

  • Property-15 Image 1
    House $626 / Nightly
    • 5Bed
    • 4Baths
    New home with an open floor plan in... Annapolis, MD

    New home with an open floor plan in the Bestgate Road neighborhood. 5 bedrooms, 3.5 Baths with a finished basement with pool table. Convenient to stores,... ...more

  • Property-16 Image 1
    House $571 / Nightly
    • 3Bed
    • 4Baths
    • (47)
    One block from City Dock, Main st,... Annapolis, MD

    One block from Naval Academy entrance. Downtown historic district. Fenced backyard. Three story historic home. Relax on the front porch and enjoy the city... ...more

  • Property-17 Image 1
    House $737 / Nightly
    • 4Bed
    • 3Baths
    Historic home across from St. John's... 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-18 Image 1
    House Select Dates for Price
    • 3Bed
    • 3Baths
    • (1) Exceptional
    Amazing home in Downtown Annapolis... Annapolis, MD

    HEART OF ANNAPOLIS HOME NIGHTLY RATE CUT IN HALF. Take part in this AMAZING end of summer deal. This beautiful home sits right downtown just blocks to the United... ...more

  • Property-19 Image 1
    Condo $520 / Nightly
    • 2Bed
    • 2Baths
    Historic downtown row home in the... Annapolis, MD

    Historic downtown row home in the heart of Annapolis with 1 off street parking spot! Updated kitchen with marble counter tops, cherry cabinets and electric... ...more

  • Property-20 Image 1
    Guest House Select Dates for Price
    • 1Bed
    • 1Baths
    • (4) Exceptional
    Charming Annapolis Guest House 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

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.