Pigeon Bay Cottages - Vacation Rentals in Maryland Quiet Waters Park

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From US $447

         

10.0 (213 Reviews)

House

PERFECT LOCATION in the heart of history

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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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 $457

         

9.8 (11 Reviews)

House

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

• Air Conditioner
• Parking
• TV

• Annapolis
• Arundel on the Bay

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From US $679

         

10.0 (202 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From US $955

         

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10.0 (3 Reviews)

House

Oasis by the Bay - Waterfront Heated Pool Hot Tub

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $392

         

|

9.6 (21 Reviews)

Bed & Breakfast

Inn at Horn Point

• Air Conditioner
• Parking
• Balcony/Terrace

• Annapolis
• Eastport

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From US $573

         

9.8 (57 Reviews)

House

Nautical Feel to This Beautiful Eastport Home

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Eastport

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From US $320

         

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10.0 (2 Reviews)

House

Skyline Sanctuary

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Annapolis
• Historic District

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From US $217

         

|

9.4 (81 Reviews)

Bed & Breakfast

Flag House Inn

• Air Conditioner
• Parking
• TV

• Annapolis
• Historic District

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From US $597

         

9.6 (19 Reviews)

House

Chesapeake Bay single family home

• Air Conditioner
• Parking
• TV

• Annapolis
• Arundel on the Bay

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From US $562

         

9.8 (58 Reviews)

House

Charming Annapolis WaterVIEW Home

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Arundel on the Bay

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From US $352

         

10.0 (241 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 US $364

         

10.0 (224 Reviews)

Cottage

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

• Air Conditioner
• Parking
• TV

• Annapolis
• Mayo

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From US $307

         

10.0 (170 Reviews)

Cottage

The Yellow Cottage on Harness Creek

• Air Conditioner
• Parking
• TV

• Annapolis
• Hillsmere

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From US $437

         

10.0 (126 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 US $296

         

10.0 (125 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 US $342

         

10.0 (96 Reviews)

House

Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Oyster Harbor

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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 $577

         

10.0 (72 Reviews)

House

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

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Eastport

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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 $420

         

10.0 (59 Reviews)

House

Eastport Cottage .5 mi from Downtown Annapolisnn

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $264

         

10.0 (57 Reviews)

Apartment

Bay View Studio Apartment

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $777

         

10.0 (54 Reviews)

House

Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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