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  • 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 just inside the main entrance. It had... ...more

    Beds: 1 Baths: 1 Property type: Room (2) Exceptional
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  • Annapolis Townhome w/Deck by Nature Trails & River

    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 worlds - a tranquil atmosphere... ...more

    Beds: 1 Baths: 2 Property type: House (0)
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  • Annapolis, ~MD~ - Lovely & Spacious Severn River Waterfront

    Annapolis, MD

    Beautifully furnished and fully equipped 4BR/4FB home with private beach & magnificent views of the Severn River. Large kitchen, living room with double sided FP, glass enclosed sun porch, & large... ...more

    Beds: 4 Baths: 4 Property type: House (0)
    $1,013 / Nightly
  • Memories on the Bay-Chesapeake Bay Waterfront Home, Pool & Hot Tub !

    Annapolis, MD

    Breathtaking....Beyond Words...You will be proud to create beautiful memories in this magnificent private estate on 1.27 acres with gorgeous panoramic views of the Chesapeake Bay and two... ...more

    Beds: 5 Baths: 6 Property type: House (6) Excellent
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  • Clean & Spacious W/ Private Entry

    Annapolis, MD

    Great local place to stay while visiting the Annapolis area; located in a safe residential neighborhood with free parking. We are close to shopping, restaurants and the Chesapeake Bay; just minutes... ...more

    Beds: 1 Baths: 1 Property type: House (11)
    $109 / Nightly
  • New Listing! Little Magothy Riverfront Home With Pool

    Annapolis, MD

    Welcome to Maryland’s Cape! Cape St. Claire, that is. A short drive to downtown Annapolis with all the peace that comes from watching the birds circle the water from the convenience of the deck or... ...more

    Beds: 3 Baths: 2 Property type: House (9) Exceptional
    $595 / Nightly
  • Annapolis Colonial - Perfect for Navy Commissioning Week

    Annapolis, MD

    Beautiful Annapolis Home - perfect for commissioning week rental. Close to the Naval Academy and the USNA golf course, this custom house is in a leafy neighborhood near the water. The house has... ...more

    Beds: 5 Baths: 4 Property type: House (0)
    $1,100 / Nightly
  • Home ideal for USNA Induction Day, Plebe Parents Weekend, and Class Reunions

    Annapolis, MD

    Beautiful single family home with finished basement located in Cape St Claire sub-division in Annapolis, Maryland. Walking distance to neighborhood park and beach (Magothy River). It's... ...more

    Beds: 5 Baths: 5 Property type: House (5) Excellent
    $639 / Nightly
  • Annapolis waterfront with a pool, on a small beach

    Annapolis, MD

    FYI, we only book 14 days a year for tax reasons, so book early! In the small community of Cape St. Claire, our home sits on 2/3 acre, overlooking the Magothy River, one of the widest rivers in... ...more

    Beds: 5 Baths: 4 Property type: House (8) Exceptional
    $1,690 / Nightly
  • Comfortable Timber Frame deep waterfront home in Annapolis close to USNA

    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 quote. Please know that the instant... ...more

    Beds: 3 Baths: 2 Property type: House (44)
    $548 / Nightly
  • Resort like living five miles from downtown!

    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 families have found our home... ...more

    Beds: 4 Baths: 4 Property type: House (0)
    $1,037 / Nightly
  • Home minutes from downtown Annapolis! Available for 2018 commissioning week!

    Annapolis, MD

    Now booking Commissioning Week 2018! Newly renovated home located just 3 miles from the heart of downtown Annapolis and USNA. Great entertaining space both inside and out! Open floor plan with new... ...more

    Beds: 4 Baths: 3 Property type: House (0)
    $1,081 / Nightly
  • Annapolis Home with Many amenities

    Annapolis, MD

    Beautiful 4 level home in water privileged community of Cape St. Claire. 4.6 miles from the Naval academy & downtown Annapolis. close to Sandy Point State Park, Annapolis Mall, Baltimore, &... ...more

    Beds: 4 Baths: 4 Property type: House (1)
    $388 / Nightly
  • Cedar Lane Farm Chateau - Your Own Private Country Club

    Annapolis, MD

    1524 YOUR OWN PRIVATE COUNTRY CLUB Incomparable Continental Waterfront Estate in Annapolis, Maryland's historic state capital! Panoramic Whitehall Creek VIEWS from most rooms! 600' of pristine... ...more

    Beds: 6 Baths: 7 Property type: House (0)
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  • Breathtaking Chesapeake Bay Waterfront From Every Room In The House !

    Annapolis, MD

    2,700 sq. ft. of casual waterfront elegance 50' from the shores of the Chesapeake bay and 15 minutes from historic downtown Annapolis and the Naval Academy... You will be so close to the Chesapeake... ...more

    Beds: 2 Baths: 2 Property type: House (3) Exceptional
    $469 / Nightly
  • Comfortable Single Family Home 3 month Min Broadneck Schools. 90 Day Min Stay Pets on a case by case basis with owner approval.

    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 Master bedroom with a private bath. 2nd... ...more

    Beds: 3 Baths: 3 Property type: House (0)
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  • Waterfront home in Arnold perfect for Commissioning Week family gatherings!

    Annapolis, MD

    Great home for large gatherings. Dining Room table seats 10. Large rooms for entertaining. A nice lawn leads down to the pier and a great view across the Little Magothy River. Rec room has a... ...more

    Beds: 3 Baths: 3 Property type: House (0)
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  • Endless views of the Chesapeake Bay. This dramatic home features soaring ceilings, spacious living areas and architectural details you should expect in a luxury home.

    Annapolis, MD

    2 month minimum. $7500/mo. Endless views of the Chesapeake Bay. This dramatic home features soaring ceilings, spacious living areas and architectural details you should expect in a luxury home.... ...more

    Beds: 4 Baths: 4 Property type: House (0)
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  • This comfortable split level home in Pendennis Mount, just across the Academy Bridge, has 2 queen beds and 2 twins and a twin in 4 bedrooms, and a couple of sofas that can be slept on.

    Annapolis, MD

    This comfortable split level home in Pendennis Mount, just across the Academy Bridge, has 2 queen beds and 2 twins and a twin in 4 bedrooms, and a couple of sofas that can be slept on. The basement... ...more

    Beds: 4 Baths: 3 Property type: House (0)
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  • Fully Furnished 4 Bedroom/3 Bathroom Single Family Home in Annapolis: This fully furnished home is located in Pendennis Mount.

    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 Bedroom/3 Bathroom Single Family Home in... ...more

    Beds: 4 Baths: 3 Property type: House (0)
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Search result 1 to 20 Of 44

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.