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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Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • Pets Allowed
View Rental
Easton
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Captains Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$323.00

Caulk`s Cove
Bozman-Neavitt
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
View Rental
Starting at (USD)

$455.00

Chesapeake Pines
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Chesapeake Pines
View Rental
Starting at (USD)

$460.00

Crabber`s Cove
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • Pets Allowed
View Rental
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 | Save 15% on June Weeks
Easton
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Gladimere Glad I`m Here
  • Pets Allowed
View Rental
Starting at (USD)

$215.00

Martini Cottage
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Martini Cottage
  • Pets Allowed
View Rental
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)

$371.00

Pandion | Save 15% on June Weeks
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pandion
  • Pets Allowed
View Rental
Starting at (USD)

$205.00

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

$305.00

Pride and Joy
Oxford
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Pride and Joy Cottage
  • Pets Allowed
View Rental
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