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Search over 150,000 vacation rentals properties now! Click here to see more Vacation Homes
Search for vacation rental homes in Chesapeake Bay
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'Sandy Pines' Lovely 4 BR Waterfront Home on Sandy Beach w/Pool, Dock — Property 314049
- House
- 4 bedrooms , sleeps 10
- 3 bathrooms
- river, waterfront
- pool
3 Nights 4 Days Waterfront Home $975S P E C I A L O F F E R- Rates (shown in USD)
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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
Fall Special - 3 nights = $1,100 TOTAL!S P E C I A L O F F E R- Rates (shown in USD)
- $1500 - $2680 per property per week
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One level family vacation home with pool, dock, sheltered cove and lots of living spaces! — Property 7004789
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $2448 - $5568 per house per week
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Blue Gates — Property 7004792
- House
- 5 bedrooms , sleeps 10
- 4 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $3712 - $4912 per house per week
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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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Budget friendly home outside St. Michaels — Property 7007434
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1513 - $3385 per house per week
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Cottage with pool, hot tub and great water — Property 7018652
- House
- 4 bedrooms , sleeps 8
- 4 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1704 - $3576 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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Beautifully appointed vacation home outside St. Michaels — Property 7022556
- House
- 6 bedrooms , sleeps 12
- 5 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $3251 - $5307 per house per week
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Sweeping Chesapeake Bay views with Sandy Beach,dock, pool. — Property 7004795
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1913 - $3998 per house per week
Refine Your Search
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Regions
- Bozman rentals (1)
- Chestertown rentals (1)
- Easton rentals (3)
- North Beach rentals (1)
- Port Republic rentals (1)
- St. Leonard rentals (1)
- St. Michaels rentals (26)
- Tilghman Island rentals (1)
Bedrooms
- 2 bedrooms (1)
- 3 bedrooms (8)
- 4+ bedrooms (26)
Sleeps
- Sleeps 5-8 (19)
- Sleeps 9-12 (13)
- Sleeps 13 or more (3)
Baths
- 1 bathroom (2)
- 2 bathrooms (9)
- 3 bathrooms (12)
- 4+ bathrooms (12)
Amenities
- air conditioning (16)
- satellite or cable tv (16)
- internet access (10)
- dishwasher (16)
- washing machine (15)
Leisure Activities
- Chesapeake Bay rentals near fishing (16)
- Chesapeake Bay rentals near golf (15)
- Chesapeake Bay rentals near skiing (1)
Suitability
- suitable for elderly or infirm (3)
- pet friendly (5)
- non smoking only (13)
