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Compare 410 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (51)

Modern Waterfront House with Amazing views!
Modern Waterfront House with Amazing views!

Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (70)

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (34)

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
10.0 out of 10, Exceptional, (113)

Your Annapolis Adventure Starts Here!!
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (138)

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chesapeake Beach

Family Beach House: Spacious Deck, Grill & Views
Family Beach House: Spacious Deck, Grill & Views
9.6 out of 10, Exceptional, (4)
The price is SAR 837
SAR 1,858 total
includes taxes & fees
28 Apr - 29 Apr

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
Mid-Century Modern on Private Beach, Designed by Award Winning Architect!
10.0 out of 10, Exceptional, (77)

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (51)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chesapeake Beach hotels
Recent reviews of Chesapeake Beach hotels

Rod 'N' Reel Resort
5/5 Excellent
"Lovely property with a great view. Peaceful visit and felt safe (traveled alone), walkable to restaurants / groceries. Friendly staff. Visit was during construction and off-season time of year. "
A verified traveler from Pleasant Gap stayed at Rod 'N' Reel Resort
Posted 3 days ago
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