Vacation Rentals & Apartments in Annapolis

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Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$476

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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Price per night from

$487

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,145

Stay just steps from the Waterfront in the modern Historic Fleet's Inn

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$405

Free parking Historic Union House Downtown with private patio

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$401

The Carrollton Cottage House

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$252

2 parking spots and Walkable to Main Street at Seashell in the City

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$465

Take your Leave of Absence around gardens with driveway parking

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$426

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Price per night from

$384

Duke's Den Downtown home with 2 PARKING spots!

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 14

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Price per night from

$639

Hanover House across from USNA Gate 3 with private back patio

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$465

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Price per night from

$458

1 Block to USNA with Chapel Views big back patio and off-site parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$465

Modern and cozy Captain’s Crossing Cape house in West Annapolis

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$402

Parking at Stunning On Cloud 9 with private patio pet-friendly

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$500

Walk to Main Street from Waterfront Condo with pool and parking

Annapolis condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$407

Family Sized Contemporary in Spacious Neighborhood

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$629

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Price per night from

$378

Cottage by the Bay on one level in family-friendly community

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

Historic Carriage House in the Heart of Downtown Annapolis

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$729

Stay at Lux Red Door Gem with 3 Parking Spots

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$382

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Price per night from

$637

Steps to Gate 1 and Free Parking at Naval-Academy Themed Home

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$610

Steps from the water, Easy parking and private backyard patio

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$355

History & Charm Near the Annapolis City Dock

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$394

Steps from USNA Gates 1 & 3 with large private patio

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$408

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Price per night from

$310

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Price per night from

$338

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Price per night from

$407

Popular Eastport Retreat - private back patio with parking and walk to USNA

Annapolis house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$785

Eastport Gem - Popular house walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$400

Deep in the Heart of Annapolis; Parking for days!

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$518

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Annapolis apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$224

"Around the corner" from everything, private backyard and parking!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$384

Eastport Bungalow - Popular house Walk to Downtown & USNA

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$400

Free Parking and Hot Tub at Pet Friendly Annapolis-themed home

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$360

Parking & Pet Friendly USNA-themed Annapolis home

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$360

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