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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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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
-
Expansive 4 bedroom home 5 blocks to town of St. Michaels, wide water views. — Property 7004814
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1265 - $2190 per house per week
-
4BR waterfront home outside Chestertown, wide water views! — Property 7004812
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- DVD
- fireplace
- Rates (shown in USD)
- $1253 - $1976 per house per week
-
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
-
Very private 25 acre home with sunset views, deep water dock, pool — Property 7004811
- House
- 4 bedrooms , sleeps 8
- 3 bathrooms
- dock boatslip
- DVD
- Rates (shown in USD)
- $1653 - $3350 per house 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
-
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
-
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
-
New House on Chesapeake Bay — Property 169538
- House
- 3 bedrooms , sleeps 8
- 2 bathrooms
- 1 half bathroom
- waterfront
- balcony
- Rates (shown in USD)
- $1100 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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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)
