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Search for vacation rental homes in Chesapeake Bay
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New upside down home overlooking Dogwood Harbor on Tilghman Island — Property 146170
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- river, waterfront
- pets considered
- Rates (shown in USD)
- $1100 - $1500 per property per week
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Chesapeake Waterfront with Dock in Crisfield, Maryland — Property 183195
- House
- 2 bedrooms , sleeps 6
- 1 bathroom
- town, waterfront
- air-conditioning
- Rates (shown in USD)
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Historic Waterfront Property in the Town of Saint Michaels — Property 254518
- House
- 6 bedrooms , sleeps 12
- 3 bathrooms
- 1 half bathroom
- waterfront
- pool
- Rates (shown in USD)
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Sunset Hill — Property 247921
- House
- 5 bedrooms , sleeps 10
- 5 bathrooms
- village, waterfront
- air-conditioning
- Rates (shown in USD)
- $2500 per property per week
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Charming, private waterfront home, close to St. Michaels, Oxford, and Easton. — Property 165697
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- river, rural
- jacuzzi
- Rates (shown in USD)
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Unique Home with Breathtaking View and Sandy Beach — Property 315763
- House
- 6 bedrooms , sleeps 11
- 3 bathrooms
- 1 half bathroom
- rural, waterfront
- garden
- Rates (shown in USD)
- $2550 per property per week
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Spacious beachfront getaway overlooking Chesapeake Bay — Property 179183
- House
- 3 bedrooms , sleeps 10
- 2 bathrooms
- beach, waterfront
- air-conditioning
- Rates (shown in USD)
- $1500 per property per week
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Charming home with bay views just short walk to the beach. — Property 187676
- House
- 3 bedrooms , sleeps 8
- 3 bathrooms
- 1 half bathroom
- beach
- balcony
- Rates (shown in USD)
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Chesapeake Bay Luxury Vacation/Rental Home — Property 156508
- House
- 6 bedrooms , sleeps 14
- 3 bathrooms
- beach, resort
- pool
- Rates (shown in USD)
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Herrington Harbour - Beautiful Single Family Home - Rose Haven — Property 186442
- House
- 3 bedrooms , sleeps 7
- 2 bathrooms
- resort, waterfront
- air-conditioning
- Rates (shown in USD)
- $1300 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 (4)
- 3 bedrooms (21)
- 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)
