Stayifyoudare - Vacation Rentals in Chesapeake Bay Bridge

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From $391

         

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 $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 $265

         

|

9.0 (34 Reviews)

House

130 m² House ∙ 3 bedrooms ∙ 6 guests

• 1399 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $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 $289

         

10.0 (97 Reviews)

Cottage

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From $358

         

|

9.6 (9 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 $342

         

New

House

130 m² House ∙ 3 bedrooms ∙ 6 guests

• 1399 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $967

         

10.0 (36 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 $204

         

|

9.4 (9 Reviews)

House

Waterfront Annapolis Home Fire Pit and Fishing Pier

• Parking
• Pet Friendly
• Accessibility

• Maryland
• Annapolis

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From $496

         

10.0 (28 Reviews)

House

Hot Tub Haven: Cozy Annapolis Backyard Oasis!

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From $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 $1,075

         

10.0 (5 Reviews)

House

Huge deck overlooking water

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From $195

         

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New

House

Walk to Lake and Boat Ramp Central Gem in Annapolis

• Parking
• Pet Friendly
• View

• Annapolis
• Cape Saint Claire

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From $341

         

10.0 (3 Reviews)

House

Charming Pet-Friendly Stay - Near Bay & Beaches.

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $484

         

10.0 (1 Review)

House

Annapolis Spacious Family Retreat

• Air Conditioner
• TV
• Balcony/Terrace

• Maryland
• Annapolis

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From $866

         

9.8 (34 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 $472

         

9.8 (23 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Maryland
• Annapolis

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From $191

         

9.6 (31 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 $478

         

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 $352

         

9.2 (40 Reviews)

House

Waterfront Annapolis Home: Fire Pit & Fishing Pier

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $984

         

7.4 (3 Reviews)

House

Luxury Waterfront Executive Family Home Annapolis with All Amenities

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $684

         

New

House

Cozy Coastal Waterfront Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Maryland
• Annapolis

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From $471

         

New

House

Annapolis Retreat

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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From $428

         

10.0 (50 Reviews)

House

Waterfront Annapolis w/swimming pool & pier -July 20-26 available

• Air Conditioner
• Parking
• Pet Friendly

• Annapolis
• Cape Saint Claire

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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 Chesapeake Bay Bridge.