View All Properties

Check out the category groups below to find your next Eastern Shore vacation rental in Maryland! Located in and around the St Michaels area, our vacation rentals offer great opportunities for exploring, adventure and relaxing. Enjoy breathtaking scenic views of the ocean and bay, hot tubs, fire pits, and beautifully cared for properties.

Guests often take advantage of nearby fishing and crabbing holes as well as the area beaches and attractions. Whether you are looking to get outdoors, see the nearby towns, or spend the days on the sand, we offer a wide variety of rentals with great amenities and features.

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.

Sort by:
Starting at (USD)

$1,287.00

Acorn Point
Easton, MD
  • 10 Guests
  • 5 Bedrooms
  • 5.5 Bathrooms
  • Code: Acorn Point
View Rental
Starting at (USD)

$425.00

Back Street Cottage
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 1.5 Bathrooms
  • Code: Back Street Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$360.00

Bay Water Cottage
Church Creek, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Bay Water Cottage
View Rental
Starting at (USD)

$465.00

Bird Dog Run
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Bird Dog Run
  • Pets Allowed
View Rental
Starting at (USD)

$1,080.00

Blue Gates
Easton, MD
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Blue Gates
View Rental
Starting at (USD)

$1,010.00

Broadwater View
Royal Oak, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Broadwater View
  • Pets Allowed
View Rental
Starting at (USD)

$600.00

Bushey Heath Farm
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 2 Bathrooms
  • Code: Bushey Heath Farm
  • Pets Allowed
View Rental
Starting at (USD)

$980.00

Captain's Cove
Saint Michaels, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
View Rental
Starting at (USD)

$481.00

Carpenter Alley Cottage
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Carpenter Alley
  • Pets Allowed
View Rental
Starting at (USD)

$355.00

Caulk's Cove
Bozman, MD
  • 7 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
View Rental
Starting at (USD)

$630.00

Cedar Cove on the Miles
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Cedar Cove on the Miles
View Rental
Starting at (USD)

$455.00

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

$550.00

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

$470.00

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

$865.00

Creek Cottage
Centreville, MD
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Creek Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$848.00

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

$547.00

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

$899.00

Fleet Street
Annapolis, MD
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Fleet Street
View Rental
Starting at (USD)

$590.00

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

$295.00

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

$770.00

Heron Point
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Heron Point
  • Pets Allowed
View Rental
Starting at (USD)

$665.00

Holland Point Preserve
Taylors Island, MD
  • 14 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: Holland Point Preserve
  • Pets Allowed
View Rental
Starting at (USD)

$1,300.00

Hudson Manor
Cambridge, MD
  • 22 Guests
  • 7 Bedrooms
  • 6 Bathrooms
  • Code: Hudson Manor
  • Pets Allowed
View Rental
Starting at (USD)

$650.00

Indian Fields
Cambridge, MD
  • 13 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Indian Fields
  • Pets Allowed
View Rental
Starting at (USD)

$735.00

Loblolly Cove
Neavitt, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
View Rental