Stayifyoudare - Vacation Rentals in Maryland World War II Memorial

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From $538

         

|

10.0 (6 Reviews)

House

Anchors Away Abode

• Air Conditioner
• Pet Friendly
• Security/Safety

• Maryland
• Annapolis

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From $449

         

10.0 (209 Reviews)

House

PERFECT LOCATION in the heart of history

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From $229

         

10.0 (46 Reviews)

Apartment

92 m² Apartment ∙ 2 bedrooms ∙ 6 guests

• 990 ft² Apartment
• Air Conditioner
• Parking
• TV

• Annapolis
• Murray Hill

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From $392

         

|

9.6 (21 Reviews)

Bed & Breakfast

Inn at Horn Point

• Air Conditioner
• Parking
• Balcony/Terrace

• Annapolis
• Eastport

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From $365

         

|

10.0 (5 Reviews)

House

Vintage Charm: Annapolis Retreat

• Air Conditioner
• Parking
• View

• Maryland
• Annapolis

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From $831

         

10.0 (198 Reviews)

House

Charming Historic Annapolis Home With Two Off-street Parking Places!

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From $430

         

10.0 (2 Reviews)

House

176 m² House ∙ 4 bedrooms ∙ 8 guests

• 1894 ft² House
• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From $234

         

|

9.4 (78 Reviews)

Bed & Breakfast

Flag House Inn

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From $320

         

|

10.0 (2 Reviews)

House

Skyline Sanctuary

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Annapolis
• Historic District

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From $570

         

9.8 (55 Reviews)

House

Nautical Feel to This Beautiful Eastport Home

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Eastport

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From $1,093

         

10.0

House

163 m² House ∙ 4 bedrooms ∙ 11 guests

• 1754 ft² House
• Air Conditioner
• Parking
• TV

• Annapolis
• Eastport

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From $280

         

10.0 (2 Reviews)

Hotel

86 State Circle - Luxury Boutique Hotel

• Air Conditioner
• Parking
• Wheelchair Accessible

• Annapolis
• Historic District

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From $263

         

|

10.0 (2 Reviews)

Apartment

USNA Home In Downtown Annapolis

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Historic District

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From $359

         

10.0 (236 Reviews)

House

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Historic District

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From $1,065

         

|

10.0 (1 Review)

House

Harrison Hall

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Annapolis
• Eastport

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From $498

         

10.0 (122 Reviews)

House

421 Irie: Simply Charming 2 Story COTTAGE! Private Pool! 1 Off Street Parking!

• Air Conditioner
• Parking
• Pool

• Annapolis
• Eastport

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From $727

         

|

10.0 (1 Review)

House

Anchors Aweigh

• Air Conditioner
• Security/Safety
• Sports/Activities

• Annapolis
• Historic District

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From $370

         

10.0 (119 Reviews)

House

Charming garden row home, easy 4 block walk to the heart of Annapolis.

• Air Conditioner
• TV
• Balcony/Terrace

• Annapolis
• Historic District

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From $426

         

|

10.0 (1 Review)

House

New! All Star Annapolis Retreat - Walk To Stadium

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Wardour

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From $437

         

10.0 (86 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 $304

         

|

10.0 (1 Review)

House

* Midcentury Modern Getaway * Prime Location *

• Air Conditioner
• Parking
• View

• Annapolis
• Historic District

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From $408

         

10.0 (86 Reviews)

Cottage

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games - Navy v. South Florida 11/15/25 weekend still available! Or the USNA Gospel Choir Concert weekend of 10/17/25

• Air Conditioner
• Parking
• TV

• Annapolis
• West Annapolis

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From $495

         

10.0 (79 Reviews)

Apartment

Waterfront Oasis of Annapolis Star

• Air Conditioner
• Parking
• Pool

• Maryland
• Annapolis

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From $884

         

10.0 (72 Reviews)

House

Charming Annapolis Victorian

• Air Conditioner
• Parking
• TV

• Annapolis
• Homewood

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Maryland World War II Memorial.