Properties with Pools

There is nothing like having your own refreshing private pool to cool off after a fun day on the water fishing, crabbing, or just sightseeing. Perfect for larger groups, many of these homes come complete with lounging and patio furniture as well as grilling tools for the perfect backyard hangout!

Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge; please inquire for more details. Also, note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambiance of the property.

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.

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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)

$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
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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
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Starting at (USD)

$980.00

Captain`s Cove
Saint Michaels, MD
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
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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)

$550.00

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

$865.00

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

$1,020.00

Crosswinds
Tilghman Island, MD
  • 12 Guests
  • 6 Bedrooms
  • 5.5 Bathrooms
  • Code: Crosswinds
  • Pets Allowed
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Starting at (USD)

$547.00

Escape Farm
Royal Oak, MD
  • 6 Guests
  • 3 Bedrooms
  • 4 Bathrooms
  • Code: Escape Farm
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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)

$770.00

Heron Point
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Heron Point
  • 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
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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
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)

$915.00

Off the Grid
Oxford, MD
  • 12 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Off the Grid
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)

$650.00

Oxford Oasis
Oxford, MD
  • 12 Guests
  • 6 Bedrooms
  • 7 Bathrooms
  • Code: Oxford Oasis
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
Neavitt, MD
  • 4 Guests
  • 2 Bedrooms
  • 1 Bathrooms
  • Code: Secret Garden
  • Pets Allowed
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Starting at (USD)

$700.00

Shore Thing
Royal Oak, MD
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Shore Thing
View Rental
Starting at (USD)

$579.50

Solitude`s Wake on Solitude Creek
Saint Michaels, MD
  • 6 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Solitude`s Wake
  • Pets Allowed
View Rental