Chesapeake Beach Vacation Rentals

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Huge Trendy Beach House w/ Yard & Beach Passes
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Huge Trendy Beach House w/ Yard & Beach Passes

4 Bedrooms
3 Bathrooms
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87 reviews
$188 - $899 / night
(excl. fees & taxes)
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Murphy Point on the Chesapeake
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Waterfront, Water All Around, Peaceful Family Getaway

3 Bedrooms
1 Bathroom
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42 reviews
$379 - $395 / night
(excl. fees & taxes)
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Tropical w/Beach Passes, Deck, Desks -Dog Friendly
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Walk to the beach, wetlands, and restaurants!

3 Bedrooms
2 Bathrooms
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149 reviews
$119 - $622 / night
(excl. fees & taxes)
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Off The Chart Stays
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Off The Chart cottage on Kent Island * New build * Accessible *Miles from wedding venues* water access

2 Bedrooms
2 Bathrooms
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7 reviews
$375 - $920 / night
(excl. fees & taxes)
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Eastport Luxe
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Newly Built 2022 Upscale Townhouse in the heart of Eastport Annapolis

3 Bedrooms
3½ Bathrooms
$500 / night
(excl. fees & taxes)
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Ivy Cove
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Newly Renovated Secluded Luxury waterfront vacation cottage with deep water pier!

3 Bedrooms
2 Bathrooms
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80 reviews
$300 - $425 / night
(excl. fees & taxes)
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Metro! Sunny Big 2 Bdrm w/ King Bed | Dog Friendly
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Metro! Sunny Big 2 Bdrm w/ King Bed | Dog Friendly

2 Bedrooms
1 Bathroom
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43 reviews
$112 - $491 / night
(excl. fees & taxes)
    1 – 7 Rentals