Girls/Guys Weekends

The Eastern Shore is a great place to reconnect with friends or take a much needed respite with your closest buddies. Shopping, golfing, spas, fabulous dining and local wineries are just a few of the activities waiting to be discovered in our quaint towns. Of course, you may want to simply relax at your waterfront property, lounge by the pool or paddle along the river. The choice is yours!

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Starting at (USD)

$557.00

Bushey Heath Farm
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • 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)

$323.00

Caulk`s Cove
Bozman-Neavitt
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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Starting at (USD)

$455.00

Chesapeake Pines
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Chesapeake Pines
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Starting at (USD)

$760.00

Heron Point
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Heron Point
  • 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
View Rental
Starting at (USD)

$756.00

Loblolly Cove
Bozman-Neavitt
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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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)

$915.00

Off the Grid
Oxford
  • 12 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Off the Grid
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Starting at (USD)

$665.00

Pines at Barrett Cove
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • 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
View Rental
Starting at (USD)

$635.00

Thistle Dew
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Thistle Dew
  • Pets Allowed
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Starting at (USD)

$850.00

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

$870.00

Town & Country
St. Michaels
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Town & Country
  • Pets Allowed
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