Fall Getaways

Enjoy the fresh, crisp fall air on MD's Eastern Shore! Local seafood and beautiful colors make fall one of the best seasons to visit!

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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)

$525.00

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)

$335.00

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
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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Starting at (USD)

$415.00

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

$505.00

Clearview
Tilghman Island, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Clearview
  • Pets Allowed
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Starting at (USD)

$425.00

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

$730.00

Emily's Lane
Wittman, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Emily`s Lane
View Rental
Starting at (USD)

$535.00

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

$395.00

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

$260.00

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)

$680.00

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)

$495.00

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

$295.00

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)

$290.00

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

$180.00

Sunflower Cottage
Oxford, MD
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Sunflower Cottage
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Starting at (USD)

$975.00

Sycamore Acres
Easton, MD
  • 12 Guests
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Code: Sycamore Acres
  • Pets Allowed
View Rental
Starting at (USD)

$475.00

The Bay House on Easy Lane
Centreville, MD
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Code: The Bay House on Easy Lane
  • Pets Allowed
View Rental
Starting at (USD)

$575.00

The Landing
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: The Landing
View Rental
Starting at (USD)

$550.00

The Water House
Saint Michaels, MD
  • 9 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: The Water House
  • Pets Allowed
View Rental