Multi Family Vacation Homes

If your idea of a vacation is reconnecting with loved ones or special friends, these properties provide just the ticket! Our larger homes sleep 10+ (please note in Talbot County 12 is the absolute maximum occupancy) and have amenities for all ages to enjoy--refreshing swimming pools, private docks for fishing, kayaks, bikes and more. Please inquire about a specific homes amenities before booking.

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Starting at (USD)

$1,675.00

Angel Cove Farm
St. Michaels
  • 10 Guests
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Code: Angel Cove Farm
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Starting at (USD)

$1,024.00

Blue Gates
Easton
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Blue Gates
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Starting at (USD)

$1,010.00

Broadwater View
Royal Oak
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Broadwater View
  • Pets Allowed
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Starting at (USD)

$1,000.00

Captain`s Cove
St. Michaels
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
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Starting at (USD)

$855.00

Creek Cottage
Centreville
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Creek Cottage
  • Pets Allowed
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Starting at (USD)

$1,125.00

Crosswinds
Tilghman Island
  • 12 Guests
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Code: Crosswinds
  • Pets Allowed
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Starting at (USD)

$615.00

Holland Point Preserve
Cambridge
  • 14 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: Holland Point Preserve
  • Pets Allowed
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Starting at (USD)

$1,300.00

Hudson Manor
Cambridge
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
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Starting at (USD)

$670.00

Indian Fields
Cambridge
  • 13 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Indian Fields
  • Pets Allowed
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Starting at (USD)

$700.00

Lovely Cove Farm
Chestertown
  • 10 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Lovely Cove Farm
  • Pets Allowed
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Starting at (USD)

$400.00

Oxbow Farm
Chestertown
  • 11 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Oxbow Farm
  • Pets Allowed
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Starting at (USD)

$570.00

PennyWhistle - St. Michaels MD
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
  • Pets Allowed
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Starting at (USD)

$525.00

Sunset Beach Cottage
Cambridge
  • 14 Guests
  • 7 Bedrooms
  • 4.5 Bathrooms
  • Code: Sunset Beach Cottage
  • Pets Allowed
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Starting at (USD)

$1,195.00

The Cove House
St. Michaels
  • 12 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: The Cove House
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Starting at (USD)

$950.00

The Dinghy
Bozman-Neavitt
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: The Dinghy
  • Pets Allowed
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Starting at (USD)

$1,194.00

Thornton Farm - Grace and Elegance
Chestertown
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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Starting at (USD)

$885.00

Tides Out
St. Michaels
  • 12 Guests
  • 6 Bedrooms
  • 3 Bathrooms
  • Code: Tides Out
  • Pets Allowed
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