Fall Cottage Getaways

Looking for a great fall getaway? These 2-3 bedroom cottages are available for a minimum of two nights after Labor Day and include complimentary early arrival and late departure (if available), as well as all other fees, bed and bath linens and pet fees (if home if pet friendly). Make plans now to be on the Eastern Shore for the best season of all! 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)

$360.00

Bay Water Cottage
Dorchester County
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
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Starting at (USD)

$427.00

Bird Dog Run
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Bird Dog Run
  • Pets Allowed
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Starting at (USD)

$529.00

Captain`s Cottage
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Captains Cottage
  • Pets Allowed
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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)

$460.00

Crabber`s Cove
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • Pets Allowed
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Starting at (USD)

$185.00

Dukes Street Cottage
Talbot County
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Dukes Street Cottage
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Starting at (USD)

$285.00

Graceful View
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Graceful View
  • Pets Allowed
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Starting at (USD)

$430.00

Mallard Point Cottage
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
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Starting at (USD)

$315.00

Memory Lane
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Memory Lane
  • Pets Allowed
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Starting at (USD)

$300.00

Oxford Beach Cottage
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Oxford Beach Cottage
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Starting at (USD)

$371.00

Pandion
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pandion
  • Pets Allowed
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Starting at (USD)

$205.00

Parlour Suite on Morris
Talbot County
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Parlour Suite on Morris
  • Pets Allowed
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Starting at (USD)

$570.00

Pines At Irish Creek
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Irish Creek
  • Pets Allowed
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Starting at (USD)

$305.00

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

$320.00

Queen Anne
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Queen Anne
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Starting at (USD)

$313.00

Red Shake Cottage
Talbot County
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Red Shake Cottage
  • Pets Allowed
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Starting at (USD)

$327.00

Red White and View
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Red White and View
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Talbot County
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Secret Garden
  • Pets Allowed
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Starting at (USD)

$315.00

Seven Pines
Talbot County
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Seven Pines
  • Pets Allowed
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Starting at (USD)

$305.00

Simplicity Cottage
Talbot County
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Simplicity Cottage
  • 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)

$334.00

Sunset Retreat
Talbot County
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathrooms
  • Code: Sunset Retreat
  • Pets Allowed
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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)

$465.00

Town Creek Haven
Talbot County
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Code: Town Creek Haven
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