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Search for vacation rental homes in Chesapeake Bay
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Sunrise~Sunset Cottage
Chesapeake Sunrise~Sunset Cottage (Fantastic Bay views) Fall Weeek end $255 — Property 317287
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- village, waterfront
- garden
- Rates (shown in USD)
- $625 per property per week
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Charming Beachfront House 50' from Water & 50 Minutes From DC Fun-Safe-Private — Property 161801
- House
- 4 bedrooms , sleeps 8
- 1 bathroom
- beach, waterfront
- air-conditioning
- Rates (shown in USD)
- $550 - $1185 per property per week
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Luxury Chesapeake Bay Waterfront - Enjoy Miles of Sandy Beach — Property 231723
- House
- 4 bedrooms , sleeps 12
- 3 bathrooms
- beach
- balcony
- Rates (shown in USD)
- $1500 per property per week
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Luxury Waterfront Home on Chesapeake Bay — Property 102015
- House
- 3 bedrooms , sleeps 6
- rural, waterfront
- air-conditioning
- Rates (shown in USD)
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Expansive 5BR home with great wide water views, pool, beautifully decorated — Property 7004818
- House
- 5 bedrooms , sleeps 10
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $2873 - $6462 per house per week
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Fantastic restored barn with expansive waterviews, pool, deep water dock — Property 7022553
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $4149 - $5649 per house per week
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RiverView
Enjoy Best Southern Maryland Waterfront Home - with Private Beach and Dock — Property 303386
- House
- 4 bedrooms , sleeps 10
- 2 bathrooms
- river, waterfront
- air-conditioning
- Rates (shown in USD)
- $1500 - $2350 per property per week
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Miles River Guest House in St Michaels — Property 263769
- House
- 2 bedrooms , sleeps 6
- 2 bathrooms
- river, waterfront
- satellite or cable
- Rates (shown in USD)
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House rental in Wittman Village Wittman - Charming Designer Decorated Retreat — Property 166854
- House
- 3 bedrooms , sleeps 6
- 1 bathroom
- 1 half bathroom
- rural, village
- pool
- Rates (shown in USD)
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Tilghman Island Victorian 1890
Tilghman Island Victorian - The Jackson House c1890 — Property 166873
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- near the ocean, town
- pool
- Rates (shown in USD)
- $900 per property per week
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Regions
- Betterton rentals (2)
- Bozman rentals (1)
- Chestertown rentals (3)
- Cobb Island rentals (1)
- Crisfield rentals (1)
- Deal Island rentals (1)
- Easton rentals (2)
- Kent Island rentals (1)
- North Beach rentals (4)
- North East rentals (5)
- Point Lookout rentals (1)
- Port Republic rentals (4)
- Solomons Island rentals (1)
- St. Leonard rentals (6)
- St. Michaels rentals (26)
- Tilghman Island rentals (5)
Bedrooms
- 2 bedrooms (3)
- 3 bedrooms (22)
- 4+ bedrooms (39)
Sleeps
- Sleeps 5-8 (39)
- Sleeps 9-12 (22)
- Sleeps 13 or more (3)
Baths
- 1 bathroom (7)
- 2 bathrooms (24)
- 3 bathrooms (20)
- 4+ bathrooms (12)
Amenities
- air conditioning (44)
- satellite or cable tv (40)
- pool (32)
- internet access (28)
- dishwasher (43)
- washing machine (41)
Leisure Activities
- Chesapeake Bay rentals near fishing (46)
- Chesapeake Bay rentals near golf (38)
- Chesapeake Bay rentals near skiing (2)
Suitability
- wheelchair accessible (2)
- suitable for elderly or infirm (14)
- pet friendly (20)
- non smoking only (38)

