Weekend Cottages

What could be better than taking a long weekend to catch your breath? Our cottages offer a chance to visit the Eastern Shore for shorter stays year round, and take in all the Eastern Shore has to offer.

Sort by:
Starting at (USD)

$360.00

Bay Water Cottage
Cambridge
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
View Rental
Starting at (USD)

$529.00

Captain`s Cottage
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)

$255.00

Cricket`s Cottage
Oxford
  • 4 Guests
  • 2 Bedrooms
  • 1.5 Bathrooms
  • Code: Crickets Watermans Cottage
  • 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
Easton
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Gladimere Glad I`m Here
  • Pets Allowed
View Rental
Starting at (USD)

$575.00

Grace Creek Cottage
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Grace Creek Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$285.00

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

$420.00

Mallard Point Cottage
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • 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)

$345.00

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

$371.00

Pandion
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)

$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)

$465.00

Town Creek Haven
Oxford
  • 8 Guests
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Code: Town Creek Haven
View Rental