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Houses Annapolis

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54 houses

Excellent Location in Downtown Annapolis- walk to everything !

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 7

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$328

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

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$550

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

Annapolis house

3 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$287

Charming and Spacious Annapolis Victorian

Annapolis house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$860

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

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$722

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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$488

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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$1,309

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 13 minutes

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$228

Stunning Home in the Heart of Downtown Annapolis

Annapolis house

3 bedrooms / 5 bathrooms / sleeps 11

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$797

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$801

Charming Annapolis Home w/ Yard - 5 Mins to Dwtn!

Annapolis house

4 bedrooms / 3 bathrooms / sleeps 10

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$303

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

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$589

New! 4 King Beds 4-min drive from Navy Stadium

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$321

Naval Academy Themed at the Gates with parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

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$449

Newly-managed Hanover House Across from Gate 3

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

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$369

New! Annapolis-themed home in Downtown Annapolis with Parking

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$182

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

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$287

Newly-Listed - USNA-themed 3 Bedroom home off West Street with parking!

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

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$115

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$408

New! Walkable Downtown Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$182

Great rentals within 20 miles that match your search

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

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$653

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

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Price per night from

$2,139

Lochhaven house for rent

Edgewater house

3 bedrooms / 1 bathroom / sleeps 2

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Price per night from

$131

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom / 1 bathroom / sleeps 2

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$59

Holistic Getaway

Bowie house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$190

Waterfront Annapolis Area 3BR/3BA Retreat with Private Pier

Edgewater house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 24 minutes

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Price per night from

$515

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$2,404

NEW! Classic Family Home: Water View, Walk to Pier

Mayo house

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 9 minutes

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$212

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$916

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$262

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

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$315

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Price per night from

$402

St. Michael's Premier in Town Summer Cottage!

St. Michaels house

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$442

KI Golf House-A PAR for the Course & Mile to Beach

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

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$459

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

Chester house

4 bedrooms / 2 bathrooms / sleeps 8

“Unbelievable value” We were a family group of 3 couples plus an infant traveling to a wedding at the Usna chapel. The home was just wonderful, had a great view, was very clean, and was well equipped for the cooking being planned. Stores, restaurants, and liquor store were close by. Easy on and off the freeway into annapolis. Scott was very personable and worked with us to make our visit just right from the moment we first contacted him about renting.

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$338

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

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Price per night from

$470

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

St. Michaels house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 34 minutes

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Price per night from

$784

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$235

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