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Compare 405 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, (54)

Modern Waterfront House with amazing views of the ChesapeakeBay!
Modern Waterfront House with amazing views of the ChesapeakeBay!

Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
10.0 out of 10, Exceptional, (73)

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (88)

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)

Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

The Lazy Crab Beach House - Free beach passes
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (47)
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
9.2 out of 10, Wonderful, (5)
The price is AED 951
AED 2,009 total
includes taxes & fees
28 May - 29 May

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, (54)
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

Wingate by Wyndham Waldorf/Washington DC Area
5/5 Excellent
"Great"
A verified traveler stayed at Wingate by Wyndham Waldorf/Washington DC Area
Posted 2 days ago
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