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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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Waterfront Home with Private Dock — Property 123352
- House
- 4 bedrooms , sleeps 8
- 2 bathrooms
- 1 half bathroom
- river, waterfront
- pool
- Rates (shown in USD)
- $1200 - $2000 per property per week
-
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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Classic Bay home with pool, dock, game room, just outside Easton and St. Michaels. — Property 7004816
- House
- 4 bedrooms , sleeps 8
- 4 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $4700 per house per week
-
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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One level vacation home outside St. Michaels, pool, wide views, great breezes — Property 7007442
- House
- 3 bedrooms , sleeps 8
- 3 bathrooms
- DVD
- fireplace
- Rates (shown in USD)
- $1744 - $3773 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
-
Treasure the Chesapeake Bay w/Beachfront Home — Property 227213
- House
- 3 bedrooms , sleeps 7
- 2 bathrooms
- beach, waterfront
- pool
- Rates (shown in USD)
- $1200 - $1600 per property per week
-
'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)
-
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
-
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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Regions
- Bozman rentals (1)
- Chestertown rentals (1)
- Easton rentals (2)
- North Beach rentals (1)
- Port Republic rentals (1)
- St. Leonard rentals (1)
- St. Michaels rentals (24)
- Tilghman Island rentals (1)
Bedrooms
- 2 bedrooms (2)
- 3 bedrooms (6)
- 4+ bedrooms (24)
Sleeps
- Sleeps 5-8 (17)
- Sleeps 9-12 (12)
- Sleeps 13 or more (3)
Baths
- 1 bathroom (2)
- 2 bathrooms (8)
- 3 bathrooms (11)
- 4+ bathrooms (11)
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)
