Old Mansions - Vacation Rentals in Chesapeake Bay Bridge

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From US $334

         

10.0 (37 Reviews)

House

Annapolis Bay House BOAT SHOW & USNA Families 2 Bedroom with Den sleeps 5

• Air Conditioner
• Parking
• TV

• Annapolis
• Cape Saint Claire

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From US $267

         

|

10.0 (4 Reviews)

Apartment

Pet-Friendly Beach Getaway, Relax by the Bay!

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $559

         

New

House

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

• Child Friendly

• Annapolis
• Cape Saint Claire

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From US $297

         

10.0 (101 Reviews)

Cottage

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $358

         

|

9.6 (10 Reviews)

Villa

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

• Air Conditioner
• Parking
• View

• Maryland
• Annapolis

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From US $1,076

         

10.0 (39 Reviews)

House

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $204

         

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9.4 (6 Reviews)

House

Waterfront Annapolis Home Fire Pit and Fishing Pier

• Parking
• Pet Friendly
• Accessibility

• Maryland
• Annapolis

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From US $827

         

10.0 (29 Reviews)

House

Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $260

         

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New

House

Annapolis Home with Deck and Whitehall Bay Access

• Air Conditioner
• Parking
• Security/Safety

• Maryland
• Annapolis

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From US $551

         

10.0 (6 Reviews)

House

Charming Pet-Friendly Stay - Near Bay & Beaches.

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $1,032

         

10.0 (5 Reviews)

House

Huge deck overlooking water

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $394

         

10.0 (1 Review)

House

Annapolis Spacious Family Retreat

• Air Conditioner
• TV
• Balcony/Terrace

• Maryland
• Annapolis

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From US $824

         

9.8 (35 Reviews)

House

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

• Air Conditioner
• Parking
• TV

• Annapolis
• Cape Saint Claire

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From US $459

         

9.8 (24 Reviews)

House

Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $466

         

9.6 (4 Reviews)

House

Walk to Lake & Boat Ramp: Central Gem in Annapolis

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $334

         

9.4 (43 Reviews)

House

Waterfront Annapolis Home: Fire Pit & Fishing Pier

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $182

         

9.4 (36 Reviews)

Apartment

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $911

         

7.4 (8 Reviews)

House

Luxury Waterfront Executive Family Home Annapolis with All Amenities

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From US $465

         

New

House

Annapolis Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $439

         

10.0 (51 Reviews)

House

Waterfront Annapolis w/swimming pool & pier

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From US $841

         

10.0 (25 Reviews)

House

Newer Waterfront Home on the Chesapeake Bay

• Air Conditioner
• Parking
• Balcony/Terrace

• Maryland
• Annapolis

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From US $310

         

10.0 (2 Reviews)

House

Renovated 3BR Home Near Sandy Point & Annapolis

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $553

         

9.8 (50 Reviews)

House

Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolisn

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From US $447

         

9.6 (79 Reviews)

House

Quiet Relaxing Waterfront Suisse Chalet

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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★ Pro Tip: Old Mansions makes it easy to compare the best listings on Old Mansions homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Old Mansions 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 Chesapeake Bay Bridge.