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  • Step Out to Main Street From a Chic Loft

    Annapolis, United States

    4.57

    Loft

    Sleeps: 4
  • Wall to Wall Cool- Filled with Original Art and Sculpture

    Annapolis, United States

    4.61

    Entire place

    Sleeps: 4
  • Our Annapolis Penthouse

    Annapolis, United States

    4.85

    Guest Suite

    Sleeps: 3
  • New Hotel Chic

    Annapolis, United States

    4.75

    Entire place

    Sleeps: 4
  • Relaxing Water Views - Mill Creek Cottage

    Annapolis, United States

    4.80

    Cottage

    Sleeps: 4
  • Brand New Reno in Historic Dist w 2 Parking spots

    Annapolis, United States

    4.71

    Condo

    Sleeps: 4
  • Stay aboard the S/V MY STUDIO on Annapolis Harbor

    Annapolis, United States

    4.71

    Boat

    Sleeps: 4
  • Cozy 2br home w/ parking in downtown Annapolis

    Annapolis, United States

    4.66

    Entire place

    Sleeps: 6
  • Annapolis Waterfront Condo - Unit #: A-203

    Annapolis, United States

    4.80

    Condo

    Sleeps: 4
  • Cape St Claire waterfront getaway

    Annapolis, United States

    5.00

    Guest Suite

    Sleeps: 2
  • Beautiful and Tranquil Carriage House

    Annapolis, United States

    4.71

    Entire place

    Sleeps: 8
  • 3BR/2BA Annapolis Cottage

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 6
  • RECENTLY RENOVATED Cottage Near Downtown Annapolis

    Annapolis, United States

    4.85

    Guesthouse

    Sleeps: 2
  • Calico Cottage Guest House, king bed, free parking

    Annapolis, United States

    4.57

    Guesthouse

    Sleeps: 2
  • Cozy Naptown Perch

    Annapolis, United States

    4.80

    Guest Suite

    Sleeps: 4
  • Centrally Located, Charming Historic Townhouse

    Annapolis, United States

    4.85

    Townhouse

    Sleeps: 8
  • ★ Midcentury Modern Getaway ★ Prime Location ★

    Annapolis, United States

    4.85

    Townhouse

    Sleeps: 6
  • Charming house; walk to everywhere in Annapolis

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 4
  • Quiet Waterfront

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 6
  • Private 2B Apt--less than 1 mi to Downtown

    Annapolis, United States

    4.75

    Guest Suite

    Sleeps: 6
  • Townhouse - 1 Mile from Downtown Strip

    Annapolis, United States

    4.75

    Townhouse

    Sleeps: 6
  • Secluded Cozy Cottage in Historic Downtown

    Annapolis, United States

    4.66

    Cottage

    Sleeps: 8
  • Charming Detached Studio w/ easy walk to Downtown.

    Annapolis, United States

    4.80

    Guest Suite

    Sleeps: 2
  • Crab Cakes and Football Historic District

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 4
  • Modern Waterfront: Quiet but close to Everything.

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 12
  • Lil’ House - A Serene Tiny Home Experience

    Annapolis, United States

    4.85

    Guesthouse

    Sleeps: 2
  • Charming Renovated Historic Home Downtown wparking

    Annapolis, United States

    4.57

    Entire place

    Sleeps: 6
  • Coastal Waterfront 1 Bedroom Cottage

    Annapolis, United States

    4.95

    Guesthouse

    Sleeps: 3
  • Historic & sunny home steps from USNA/downtown

    Annapolis, United States

    5.00

    Entire place

    Sleeps: 7
  • Luxury Waterfront Annapolis/ Private Beach & Dock

    Annapolis, United States

    5.00

    Entire place

    Sleeps: 6
  • Garden View, a spacious 1 bedroom with loft.

    Annapolis, United States

    5.00

    Guest Suite

    Sleeps: 5
  • Private Art-Filled Guesthouse near Naval Academy

    Annapolis, United States

    5.00

    Guesthouse

    Sleeps: 2
  • Chesapeake Comfort, Annapolis.

    Annapolis, United States

    4.75

    Entire place

    Sleeps: 6
  • New Downtown Annapolis Condo With Free Parking

    Annapolis, United States

    4.90

    Condo

    Sleeps: 4
  • Old Orchard Cottage

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 4
  • Charming Cottage 2 parking spot easy walk downtown

    Annapolis, United States

    4.66

    Cottage

    Sleeps: 6
  • Sophisticated & Spacious Historic Home w/ Parking!

    Annapolis, United States

    4.75

    Entire place

    Sleeps: 6
  • Gorgeous Historic Downtown Annapolis House

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 12
  • The Crow's Nest - Excellent downtown Annapolis Apt

    Annapolis, United States

    4.66

    Condo

    Sleeps: 3
  • Condo Houseboat

    Annapolis, United States

    4.90

    Houseboat

    Sleeps: 4
  • Perfect Eastport location

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 4
  • Waterfront farm retreat for vacation & telework

    Annapolis, United States

    4.85

    Cottage

    Sleeps: 7
  • Cozy Annapolis Cottage.

    Annapolis, United States

    4.85

    Entire place

    Sleeps: 6
  • Historic Downtown in-law suite

    Annapolis, United States

    4.75

    Entire place

    Sleeps: 3
  • Historic 3 Bedroom Downtown Annapolis Townhome

    Annapolis, United States

    4.80

    Townhouse

    Sleeps: 6
  • Moose’s Happy Place

    Annapolis, United States

    5.00

    Townhouse

    Sleeps: 8
  • Great reviews! Pool, DT, stadium, goats, and more!

    Annapolis, United States

    4.75

    Guest Suite

    Sleeps: 6
  • The Navy House-Walk or Shuttle Downtown! 3 bd

    Annapolis, United States

    4.75

    Entire place

    Sleeps: 7
  • One bedroom apartment in Annapolis

    Annapolis, United States

    4.90

    Entire place

    Sleeps: 4
  • Boutique Historic Home Steps from the State House!

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 8
  • Charming Downtwn Home, Private Parking Patio&Yard!

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 10
  • Annapolis Downtown Pleasant St Townhome 3 bedrooms

    Annapolis, United States

    4.57

    Townhouse

    Sleeps: 6
  • Beautiful Downtown Annapolis Home!

    Annapolis, United States

    4.90

    Townhouse

    Sleeps: 6
  • CIRCA 1885-Historic Annapolis-USNA GATE 1

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 5
  • Charming lower-level apartment in Annapolis

    Annapolis, United States

    4.80

    Entire place

    Sleeps: 2
  • Green On Fleet - Rowhouse in Historic Annapolis

    Annapolis, United States

    4.85

    Entire place

    Sleeps: 4
  • LOCATION!! Steps away from historic Main Street.

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 6
  • Miller Cottage - near Navy Stadium

    Annapolis, United States

    4.95

    Cottage

    Sleeps: 4
  • Burley on the Bay

    Annapolis, United States

    4.95

    Entire place

    Sleeps: 12
  • Weems Creek Cottage, Annapolis Waterfront

    Annapolis, United States

    4.90

    Cottage

    Sleeps: 4
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