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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, (51)

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, (71)

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)

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 AED 624
AED 1,611 total
includes taxes & fees
7 May - 8 May

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

Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (244)
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

Inn at Perry Cabin
5/5 Excellent
"Our stay here was excellent. The highlight was arguably the check-in, where we were surprised with a birthday welcome, as well as a little onesie for our soon to arrive baby girl. This was a birthday/baby moon trip and we shared this info prior to arrival, and the staff was incredible in providing us with the warmest welcome we've ever had. We will definitely be back. "
A verified traveler stayed at Inn at Perry Cabin
Posted 2 days ago
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