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Search Cottages in Chesapeake Beach

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May 2 - May 4
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May 9 - May 11
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May 23 - May 25
In two months
Jun 20 - Jun 22

Compare 30 Cottages in Chesapeake Beach with updated reviews, rates, and availability.

Pet-friendly Annapolis Home: Walk to Beach!
Interior

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Interior

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
10.0 out of 10, Exceptional, (1)
"It really is an adorable cottage, very tastefully decorated.the owner provided a very thoughtful gift basket on arrival. I would recommend this cottage to anyone."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Annapolis Home Near Beach & Quiet Waters Park!
Interior

Annapolis Home Near Beach & Quiet Waters Park!

3.0 star property
Annapolis Home Near Beach & Quiet Waters Park!
Updated North Beach Cottage: Pet Friendly!
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Updated North Beach Cottage: Pet Friendly!

3.0 star property
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Property grounds

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Tranquil Port Republic Home w/ Water Views!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
North Beach Cottage - Walk to Chesapeake Bay
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
North Beach Cottage - Walk to Chesapeake Bay
Bayfront Gem w/ Amazing Water Views + Pond!
House (3 Bedrooms) | Interior

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Interior

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Family-friendly Chesapeake Beach House With Deck!
House (1 Bedroom) | Living area | Books

Family-friendly Chesapeake Beach House With Deck!

3.0 star property
6.0 out of 10, (1)
Family-friendly Chesapeake Beach House With Deck!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
7 bedrooms, iron/ironing board, bed sheets

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Interior

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

3.0 star property
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Water-view Deale Home: Walk to Marina, Restaurants
Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
Maryland Vacation Rental w/ Private Pool & Dock
Interior

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock
Maryland Vacation Rental: Walk to Beach
House (2 Bedrooms) | Private kitchen | Paper towels

Maryland Vacation Rental: Walk to Beach

3.0 star property
Maryland Vacation Rental: Walk to Beach
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Outdoor spa tub

Annapolis Vacation Home: 2 Mi to Quiet Waters Park

3.0 star property
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Tilghman Island Retreat By Knapps Narrows!
Interior

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Coastal Edgewater Home w/ Private Hot Tub!
Interior

Coastal Edgewater Home w/ Private Hot Tub!

3.0 star property
Coastal Edgewater Home w/ Private Hot Tub!
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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