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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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Light Filled Contemporary with 4 Queen bedrooms, dock,pool — Property 7004815
- House
- 4 bedrooms , sleeps 9
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1747 - $3776 per house per week
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Fantastic Family Compound 1/2 mile to St. Michaels, Pool, Dock, Hot tub — Property 7004796
- House
- 5 bedrooms , sleeps 10
- 4 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $2839 - $6271 per house per week
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Restored farmhouse with pool, poolhouse, dock, kayak and more! — Property 7004804
- House
- 5 bedrooms , sleeps 10
- 4 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $2895 - $5407 per house per week
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Upscale home outside St. Michaels, pool, dock, newly renovated kitchen and baths, a fabulous retreat — Property 7004819
- House
- 6 bedrooms , sleeps 11
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $2850 - $5362 per house per week
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Large Luxury Waterfront Cape Cod with New Pool and Beautiful Sunsets — Property 233398
- House
- 5 bedrooms , sleeps 12
- 4 bathrooms
- town, waterfront
- pool
- Rates (shown in USD)
- $3000 - $5850 per property 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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'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
- Rates (shown in USD)
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Waterfront @ Southeast Creek
Cozy up by the Big Stone Fireplace For the Holidays and Enjoy the Waterviews — Property 254204
- House
- 6 bedrooms , sleeps 12
- 6 bathrooms
- rural, waterfront
- garden
- Rates (shown in USD)
- $2695 - $5495 per property 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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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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Regions
- Bozman rentals (1)
- Chestertown rentals (1)
- St. Michaels rentals (10)
Baths
- 2 bathrooms (1)
- 3 bathrooms (4)
- 4+ bathrooms (7)
Amenities
- air conditioning (6)
- satellite or cable tv (6)
- internet access (4)
- dishwasher (6)
- washing machine (5)
Leisure Activities
- Chesapeake Bay rentals near fishing (6)
- Chesapeake Bay rentals near golf (6)
- Chesapeake Bay rentals near skiing (1)
