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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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Chesapeake Bay Vacation Rental, quiet, beachy, open, bay view — Property 119031
- House
- 4 bedrooms , sleeps 12
- 2 bathrooms
- 1 half bathroom
- beach, near the ocean
- balcony
$500 Fall Weekend Getaway special!!!S P E C I A L O F F E R- Rates (shown in USD)
- $1200 - $1500 per property per week
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Osprey's Nest
Spacious,Peaceful,Comfort. Bay View,Eagles,Osprey,Sunrises from deck,Beaches — Property 248526
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- beach, rural
- balcony
Fall Getaway Special 40% off peak ratesS P E C I A L O F F E R- Rates (shown in USD)
- $2000 - $2500 per property per week
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Budget friendly cottage getaway, with rowboat included! — Property 7022552
- Cottage
- 4 bedrooms , sleeps 8
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1315 - $1940 per cottage 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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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
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90 acre farm with wrap around views, 5 minutes to St. Michaels, pool, dock — Property 7004794
- House
- 4 bedrooms , sleeps 8
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1453 - $3325 per house per week
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Conveniently located home between Easton and St. Michaels, private with Tred Avon views! — Property 7015502
- Cottage
- 3 bedrooms , sleeps 6
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1375 - $2275 per cottage per week
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Tilghman Island getaway with private dock, great views, and more! — Property 7007436
- Cottage
- 3 bedrooms , sleeps 6
- 2 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1570 per cottage per week
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Charming Tilghman Island getaway cottage — Property 7007441
- Cottage
- 4 bedrooms , sleeps 8
- 2 bathrooms
- DVD
- fireplace
- Rates (shown in USD)
- $1060 - $1310 per cottage per week
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Fun house outside St. Michaels, pool, dock, hot tub, ping pong — Property 7007440
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1473 - $3345 per house per week
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Regions
- Betterton rentals (3)
- Bozman rentals (1)
- Chestertown rentals (3)
- Church Creek rentals (1)
- Cobb Island rentals (1)
- Crisfield rentals (3)
- Deal Island rentals (2)
- Deale Beach rentals (1)
- Easton rentals (3)
- Kent Island rentals (1)
- North Beach rentals (4)
- North East rentals (6)
- Point Lookout rentals (1)
- Port Republic rentals (5)
- Solomons Island rentals (2)
- St. Leonard rentals (9)
- St. Michaels rentals (44)
- Tilghman Island rentals (9)
Bedrooms
- 2 bedrooms (9)
- 3 bedrooms (42)
- 4+ bedrooms (48)
Sleeps
- Sleeps 1-4 (2)
- Sleeps 5-8 (66)
- Sleeps 9-12 (26)
- Sleeps 13 or more (5)
Baths
- 1 bathroom (13)
- 2 bathrooms (43)
- 3 bathrooms (28)
- 4+ bathrooms (13)
Lodging Type
- cabin rentals (1)
- condo rentals (2)
- cottage rentals (24)
- estate rentals (4)
- farmhouse rentals (2)
- house rentals (64)
- lodge rentals (1)
- villa rentals (1)
Amenities
- air conditioning (62)
- satellite or cable tv (57)
- pool (45)
- internet access (39)
- dishwasher (59)
- washing machine (56)
Leisure Activities
- Chesapeake Bay rentals near fishing (65)
- Chesapeake Bay rentals near golf (54)
- Chesapeake Bay rentals near skiing (3)
Suitability
- wheelchair accessible (5)
- suitable for elderly or infirm (22)
- pet friendly (26)
- non smoking only (57)
