Hawaii Beach Comber - Vacation Rentals in Annapolis Mall Shopping Center

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From US $534

         

10.0 (113 Reviews)

House

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

• Air Conditioner
• Parking
• Pool

• Annapolis
• Cape St. John

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From US $365

         

|

10.0 (5 Reviews)

House

Vintage Charm: Annapolis Retreat

• Air Conditioner
• Parking
• View

• Maryland
• Annapolis

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From US $411

         

10.0 (3 Reviews)

Hotel

86 State Circle - Luxury Boutique Hotel

• Air Conditioner
• Parking
• Wheelchair Accessible

• Annapolis
• Historic District

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From US $430

         

10.0 (89 Reviews)

House

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $263

         

|

10.0 (2 Reviews)

Apartment

USNA Home In Downtown Annapolis

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Historic District

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From US $140

         

|

9.4 (1010 Reviews)

Hotel

Graduate by Hilton Annapolis

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $321

         

10.0 (87 Reviews)

Cottage

Your Annapolis Waterfront retreat - ready for a December or January Annapolis getaway! Midnight Madness Downtown Annapolis -Dec 18 , or Getaway music weekend? Check out Ram's Head On Stage!

• Air Conditioner
• Parking
• TV

• Annapolis
• West Annapolis

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From US $426

         

|

10.0 (1 Review)

House

All Star Annapolis Retreat - Walk To Stadium

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Wardour

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From US $110

         

|

9.4 (44 Reviews)

Hotel

TownePlace Suites by Marriott Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Parole

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From US $861

         

10.0 (73 Reviews)

House

Charming Annapolis Victorian

• Air Conditioner
• Parking
• TV

• Annapolis
• Homewood

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From US $311

         

10.0 (72 Reviews)

House

Cozy 2br home w/parking in downtown Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From US $495

         

10.0 (70 Reviews)

House

Recently Renovated Annapolis Home - Conveniently Located

• Air Conditioner
• Parking
• TV

• Annapolis
• Murray Hill

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From US $463

         

10.0 (48 Reviews)

Apartment

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $883

         

10.0 (35 Reviews)

House

West Annapolis Cottage

• Air Conditioner
• Parking
• TV

• Annapolis
• West Annapolis

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From US $617

         

10.0 (35 Reviews)

House

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $528

         

10.0 (34 Reviews)

House

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From US $297

         

10.0 (34 Reviews)

House

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

• Air Conditioner
• Parking
• TV

• Annapolis
• Murray Hill

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From US $290

         

10.0 (34 Reviews)

Condo

New Downtown Annapolis Condo With Free Parking

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Murray Hill

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From US $864

         

10.0 (33 Reviews)

House

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From US $558

         

10.0 (30 Reviews)

House

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

• Air Conditioner
• TV
• Balcony/Terrace

• Annapolis
• Historic District

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From US $507

         

10.0 (25 Reviews)

House

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

• Air Conditioner
• TV
• Balcony/Terrace

• Annapolis
• Historic District

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From US $133

         

10.0 (24 Reviews)

Apartment

New Loft w/South River view from treehouse deck!

• Air Conditioner
• Parking
• TV

• Maryland
• Riva

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From US $399

         

10.0 (22 Reviews)

House

Historic 3 Bedroom Downtown Annapolis Townhome

• Air Conditioner
• Pet Friendly
• TV

• Annapolis
• Historic District

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From US $178

         

10.0 (22 Reviews)

Apartment

Tranquility Awaits

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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