Fall Weekend Getaways

There is nothing like the crisp air, the delicious seafood and lazy pace of Fall on the Eastern Shore. Enjoy one of our delightful autumn festivals, or make plans to reconnect with friends or family with a cottage getaway.

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Starting at (USD)

$425.00

Back Street Cottage
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Back Street Cottage
  • Pets Allowed
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Starting at (USD)

$360.00

Bay Water Cottage
Church Creek, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
View Rental
Starting at (USD)

$600.00

Bushey Heath Farm
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • Pets Allowed
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Starting at (USD)

$481.00

Carpenter Alley Cottage
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Carpenter Alley
  • Pets Allowed
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Starting at (USD)

$355.00

Caulk's Cove
Bozman, MD
  • 7 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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Starting at (USD)

$455.00

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

$470.00

Crabber's Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • Pets Allowed
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Starting at (USD)

$547.00

Escape Farm
Royal Oak, MD
  • 6 Guests
  • 3 Bedrooms
  • 4 Bathrooms
  • Code: Escape Farm
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Starting at (USD)

$430.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
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Starting at (USD)

$305.00

Memory Lane
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Memory Lane
  • Pets Allowed
View Rental
Starting at (USD)

$360.00

Oxford Beach Cottage
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Oxford Beach Cottage
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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)

$740.00

Pines at Barrett Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
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Starting at (USD)

$530.00

Pines At Irish Creek
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Irish Creek
  • Pets Allowed
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Starting at (USD)

$335.00

Pride and Joy
Oxford, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pride and Joy Cottage
  • Pets Allowed
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Starting at (USD)

$350.00

Red Shake Cottage
Oxford, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Red Shake Cottage
  • Pets Allowed
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Starting at (USD)

$395.00

Red White and View
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Red White and View
  • Pets Allowed
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Starting at (USD)

$335.00

Simplicity Cottage
Tilghman Island, MD
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Simplicity Cottage
  • Pets Allowed
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Starting at (USD)

$585.00

Sunrise Cove
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
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Starting at (USD)

$595.00

Swan's Rest
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Swans Rest
  • Pets Allowed
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Starting at (USD)

$880.00

Town & Country
Saint Michaels, MD
  • 10 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Town & Country
  • Pets Allowed
View Rental