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Search for vacation rental homes in Chesapeake Bay
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Beach House at Little River
Top of the Chesapeake - Minutes from Historic Charlestown — Property 174163
- House
- 5 bedrooms , sleeps 11
- 2 bathrooms
- river, waterfront
- balcony
- Rates (shown in USD)
- $2090 - $2250 per property per week
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St Michael
Fresh & Brand New: - 3 night fall special! Also free sailing adventure! — Property 257093
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- 1 half bathroom
- resort, town
- pool
- Rates (shown in USD)
- $1500 - $2680 per property per week
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Victorian Tilghman 3/4 bedroom
Victorian Tilghman Island 3/4 Bedroom House — Property 258777
- House
- 3 bedrooms , sleeps 6
- 3 bathrooms
- beach, river
- balcony
- Rates (shown in USD)
- $1100 per property per week
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Peaceful, Waterfront Estate w/Pier (close to St. Michaels & Annapolis) — Property 316300
- House
- 4 bedrooms , sleeps 8
- 2 bathrooms
- waterfront
- garden
- Rates (shown in USD)
- $1260 - $1960 per property per week
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Private 9-Acre Waterfront Home on the Elk River — Property 227532
- House
- 4 bedrooms , sleeps 10
- 2 bathrooms
- 1 half bathroom
- river, rural
- pets considered
- Rates (shown in USD)
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ENDLESS SUNSETS
Endless Waterfront Sunsets on Eastern Bay!! — Property 246578
- House
- 3 bedrooms , sleeps 8
- 3 bathrooms
- 1 half bathroom
- village, waterfront
- garden
- Rates (shown in USD)
- $2500 per property per week
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Quaint Beach House In Thriving and Walkable Beach Community — Property 157111
- House
- 2 bedrooms , sleeps 6
- 1 bathroom
- beach, resort
- garden
- Rates (shown in USD)
- $1000 per property per week
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Comfortable, well-equipped home in quiet seaside town. Easy drive to Chestertown — Property 186924
- House
- 3 bedrooms , sleeps 6
- 1 bathroom
- 1 half bathroom
- beach, river
- pets considered
- Rates (shown in USD)
- $700 - $1050 per property per week
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Charming home in beach community of Upper Eastern Shore on Chesapeake Bay — Property 235930
- House
- 6 bedrooms , sleeps 11
- 2 bathrooms
- beach, town
- pets considered
- Rates (shown in USD)
- $850 per property per week
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Charming 2 story dutch colonial on the Chesapeake Bay — Property 138016
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- waterfront
- pets considered
- Rates (shown in USD)
- $1000 - $1500 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)
