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
Talbot County
  • 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
Talbot County
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
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Starting at (USD)

$323.00

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

$455.00

Chesapeake Pines
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Chesapeake Pines
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Starting at (USD)

$760.00

Heron Point
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Heron Point
  • Pets Allowed
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Starting at (USD)

$739.00

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

$1,300.00

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

$670.00

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

$756.00

Loblolly Cove
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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Starting at (USD)

$915.00

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

$665.00

Pines at Barrett Cove
Talbot County
  • 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
Dorchester County
  • 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
Talbot County
  • 12 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: The Cove House
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Starting at (USD)

$635.00

Thistle Dew
Talbot County
  • 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
Kent County
  • 11 Guests
  • 6 Bedrooms
  • 4.5 Bathrooms
  • Code: Thornton
  • Pets Allowed
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Starting at (USD)

$870.00

Town & Country
Talbot County
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Town & Country
  • Pets Allowed
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