Multi Family 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. From refreshing swimming pools to private docks for fishing, kayaks, bikes and much more. Check out the selection of our multi-family vacation homes in the Chesapeake Bay area and please inquire about a specific homes amenities before booking.

Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

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Starting at (USD)

$1,287.00

Acorn Point
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Acorn Point
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Starting at (USD)

$1,080.00

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

$1,010.00

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

$980.00

Captain's Cove
Saint Michaels, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
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Starting at (USD)

$865.00

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

$1,020.00

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

$665.00

Holland Point Preserve
Taylors Island, MD
  • 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, MD
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
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Starting at (USD)

$650.00

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

$735.00

Loblolly Cove
Neavitt, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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Starting at (USD)

$650.00

Oxford Oasis
Oxford, MD
  • 12 Guests
  • 6 Bedrooms
  • 7 Bathrooms
  • Code: Oxford Oasis
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Starting at (USD)

$540.00

PennyWhistle
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
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Starting at (USD)

$1,045.00

Thornton Farm - Grace and Elegance
Chestertown, MD
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Tricefields
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Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Waverly
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Starting at (USD)

$1,215.00

Willoughby
Cambridge, MD
  • 24 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Willoughby
  • Pets Allowed
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Starting at (USD)

$1,225.00

Woodwind
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Woodwind
  • Pets Allowed
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