St. Michaels

These vacation homes are all convenient to historic St. Michaels, Maryland to enjoy dining, shopping, and sight-seeing. Please note prices given below are per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Less than weekly stays are typically a higher nightly rate and prices will vary based upon season and 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)

$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)

$1,430.00

Bonnie Breeze
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 4.5 Bathrooms
  • Code: Bonnie Breeze
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)

$470.00

Crabber's Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • Pets Allowed
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)

$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)

$735.00

Loblolly Cove
Neavitt, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
View Rental
Starting at (USD)

$430.00

Mallard Point Cottage
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallard Point Cottage
  • Pets Allowed
View Rental
Starting at (USD)

$620.00

Mallard's Landing
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallards Landing
  • Pets Allowed
View Rental
Starting at (USD)

$590.00

Osprey Point
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Osprey Point
  • Pets Allowed
View Rental
Starting at (USD)

$540.00

PennyWhistle
McDaniel, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
View Rental
Starting at (USD)

$740.00

Pines at Barrett Cove
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
View Rental
Starting at (USD)

$350.00

Queen Anne
Easton, MD
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Queen Anne
View Rental
Starting at (USD)

$395.00

Red White and View
Easton, MD
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Red White and View
  • Pets Allowed
View Rental
Starting at (USD)

$585.00

Sunrise Cove
Saint Michaels, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
View Rental
Starting at (USD)

$595.00

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