33 Properties in Chesapeake Beach, Maryland, United States of America. June 7, 2026 through June 8, 2026

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Stays within a 15-minute walk to the beach

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Rod n Reel Charter Fishing

Breezy Point Beach

Chesapeake Beach Water Park

Chesapeake Beach Railway Museum

Bruce Gabrielson's Surf Art Gallery and Museum

Brownies Beach

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Chesapeake Beach

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WoodSpring Suites

TownePlace Suites

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Country Inn & Suites - by Choice Hotels

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avid hotels

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Enjoy the season with activities like ice skating, snowmobiling, or sledding.

Scuba diving or snorkeling

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Tennis

Casino

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33 properties

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A bathroom with a large bathtub, a vanity with a mirror, and a window.

A room with a view of a wooden deck and a gazebo by the water.

Inn at Perry Cabin

Restaurant

Spa

Bar and lounge

Restaurant, Spa, Bar and lounge

9.69.6 out of 10

Exceptionalexceptional

398 reviews(398 reviews)

$1,170 nightly

The current price is $1,287 total

$1,287 total

Total with taxes and fees

We have 1 left at this price

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A dining area with a wooden ceiling, a fireplace, and a white mantelpiece.

A spacious living room with a fireplace, a television, and a dining area with a table and chairs.

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Entire home by Vrbo

Sleeps 6 · 3 bedrooms · 2 bathrooms

Internet

Dryer

AC, Internet, Dryer

1010 out of 10

Exceptionalexceptional

$435 nightly

The current price is $891 total

$891 total

Total with taxes and fees

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An outdoor deck with a covered grill, a table and chairs, and a white fence.

A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

Annapolis Retreat - 7 mins from downtown Annapolis!

Entire home by Vrbo

Sleeps 9 · 5 bedrooms · 2 bathrooms

Barbecue grill

Onsite parking

Barbecue grill, AC, Onsite parking

1010 out of 10

Exceptionalexceptional

6 reviews(6 reviews)

$420 nightly

The current price is $858 total

$858 total

Total with taxes and fees

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Photo gallery for Inn at Perry Cabin

Inn at Perry Cabin

Photo gallery for Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Photo gallery for Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!