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Compare 77 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Cozy Cottage with access to and partially obstructed views of the bay.
Cozy Cottage with access to and partially obstructed views of the bay.
9.4 out of 10, Exceptional, (18)

Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (221)

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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (176)

Eastern Shore Waterside Cottage Near St. Michaels
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (19)

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (207)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (117)

Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
9.8 out of 10, Exceptional, (29)
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 660
SAR 1,674 total
includes taxes & fees
5 May - 6 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, (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

SpringHill Suites by Marriott Annapolis
5/5 Excellent
"I would go back to this hotel. "
A verified traveler stayed at SpringHill Suites by Marriott Annapolis
Posted 3 days ago
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