Monthly Rentals

Looking for a longer term rental? Many of our properties do offer monthly rentals from October to May. Monthly pricing ranges from $2500-$5000 per month, and do not include housekeeping or linens during your stay. Please inquire for more information regarding our monthly rental program. Monthly rentals are subject to final approval by of the homeowner.

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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)

$529.00

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

$460.00

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

$185.00

Dukes Street Cottage
Easton
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Dukes Street Cottage
View Rental
Starting at (USD)

$480.00

Easton Hideaway
Easton
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Easton Hideaway
  • Pets Allowed
View Rental
Starting at (USD)

$580.00

Gladimere
Easton
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Gladimere Glad I`m Here
  • Pets Allowed
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Starting at (USD)

$215.00

Martini Cottage
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Martini Cottage
  • Pets Allowed
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Starting at (USD)

$315.00

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

$345.00

Middle Point Cottage
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 1 Bathrooms
  • Code: Middle Point Cottage
  • Pets Allowed
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Starting at (USD)

$371.00

Pandion
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pandion
  • Pets Allowed
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Starting at (USD)

$205.00

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

$305.00

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

$313.00

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

$327.00

Red White and View
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Red White and View
View Rental
Starting at (USD)

$315.00

Seven Pines
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Seven Pines
  • Pets Allowed
View Rental
Starting at (USD)

$305.00

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

$583.00

Sunrise Cove
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
View Rental
Starting at (USD)

$590.00

Swan`s Rest
Easton
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Swans Rest
  • Pets Allowed
View Rental