Stayifyoudare - Vacation Rentals in Annapolis Harbour Center

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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 $307

         

10.0 (168 Reviews)

Cottage

The Yellow Cottage on Harness Creek

• Air Conditioner
• Parking
• TV

• Annapolis
• Hillsmere

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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 $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 $365

         

|

10.0 (5 Reviews)

House

Vintage Charm: Annapolis Retreat

• Air Conditioner
• Parking
• View

• Maryland
• Annapolis

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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 $781

         

10.0 (2 Reviews)

House

203 m² House ∙ 5 bedrooms ∙ 10 guests

• 2187 ft² House
• Air Conditioner
• TV
• View

• Annapolis
• Hillsmere

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From $213

         

|

9.4 (1011 Reviews)

Hotel

Graduate by Hilton Annapolis

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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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 $511

         

10.0 (108 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 $365

         

10.0 (1 Review)

House

241 m² House ∙ 5 bedrooms ∙ 12 guests

• 2594 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Parole

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From $130

         

|

9.4 (29 Reviews)

Hotel

TownePlace Suites by Marriott Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Parole

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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 $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 $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 $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 $416

         

|

10.0 (1 Review)

House

New! Golden Anchor Retreat Lux Living!

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Edgewater

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From $884

         

10.0 (72 Reviews)

House

Charming Annapolis Victorian

• Air Conditioner
• Parking
• TV

• Annapolis
• Homewood

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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 $320

         

10.0 (71 Reviews)

House

Cozy 2br home w/parking in downtown Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From $242

         

|

10.0 (1 Review)

House

London Towne Bungalow Wloft - Walk To The Beach!

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Edgewater

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From $562

         

10.0 (69 Reviews)

House

Recently Renovated Annapolis Home - Conveniently Located

• Air Conditioner
• Parking
• TV

• Annapolis
• Murray Hill

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From $420

         

10.0 (56 Reviews)

House

Eastport Cottage .5 mi from Downtown Annapolisnn

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From $662

         

10.0 (51 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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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 Annapolis Harbour Center.