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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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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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North Beach Vacation Home — Property 242309
- House
- 3 bedrooms , sleeps 6
- 2 bathrooms
- 1 half bathroom
- beach, waterfront
- jacuzzi
- Rates (shown in USD)
- $1400 per property per week
-
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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Chesapeake Bay Waterfront Luxury Vacation Home Near Solomon's Island — Property 122821
- House
- 3 bedrooms , sleeps 10
- 3 bathrooms
- beach, waterfront
- pets considered
- Rates (shown in USD)
- $1550 per property per week
-
Lighthouse Replica Home Right on the Water — Property 154370
- House
- 4 bedrooms , sleeps 8
- 4 bathrooms
- beach, waterfront
- jacuzzi
- Rates (shown in USD)
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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
-
Magical Bayfront Home — Property 212770
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- beach, waterfront
- pets considered
- Rates (shown in USD)
- $1800 - $2500 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)
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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)

