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Houses Annapolis

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53 houses

Annapolis Area Waterfront Home

Annapolis house

5 bedrooms / 4 bathrooms / sleeps 11

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Price per night from

$662

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

$857

Annapolis House w/ Patio in Bay Ridge Maryland!

Annapolis house

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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$859

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

$486

The Heart of Historic Cool in Annapolis

Annapolis house

5 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$1,151

Cozy Home in Historic Annapolis with Parking

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 40 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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Price per night from

$796

Charming Annapolis Waterview home

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$801

Charming Townhouse - Steps to City Dock and USNA

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 58 minutes

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Price per night from

$520

New - Play at the beach just minutes to downtown Annapolis

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$381

Newly furnished home, perfect for Naval Academy Football games!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

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$369

New Luxury Home Walkable to Main Street w Parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

New Lux Downtown Annapolis Home with 3 parking spots!

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$369

Spend the night in Historic Downtown Annapolis

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$369

Naval Academy Themed at the Gates with parking!

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$524

New! Steps to Main Street with views of the Capital

Annapolis house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$289

Annapolis-themed home in Downtown Annapolis with Parking

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

Renovated Eastport Firehouse in Annapolis

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$287

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

Annapolis house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$232

Historic Charm! Walk to Annapolis Waterfront & Academy

Annapolis house

3 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 4 minutes

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$575

Walkable to Downtown Annapolis

Annapolis house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 4 minutes

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Price per night from

$182

Great rentals within 20 miles that match your search

Private Room Close To Baltimore and BWI Airport + EXTRAS

Glen Burnie house

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$59

Bay Cottage Resort

St. Michaels house

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$2,404

Clean & Spacious

Cape Saint Claire house

4 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$917

Wellspring Manor & Spa

Largo house

5 bedrooms / 8 bathrooms / sleeps 10

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Price per night from

$1,839

Bayside Retreat

Rock Hall house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$258

Holistic Getaway

Bowie house

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$167

Bay Cottage

Rock Hall house

2 bedrooms / 1 bathroom / sleeps 5

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Price per night from

$312

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

$782

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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$337

Responds fast! avg. 27 minutes

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Price per night from

$400

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$514

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

$440

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

$486

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Shady Side house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$478

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$236

Waterfront Annapolis Home: Fire Pit & Fishing Pier

Cape Saint Claire house

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 48 minutes

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Price per night from

$332

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