Vacation Rentals with Pools

There is nothing like having your own refreshing pool to cool off after a fun day on the water fishing, crabbing, or just sight seeing. Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge. Please inquire. Also note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambience 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)

$427.00

Bird Dog Run
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Bird Dog Run
  • Pets Allowed
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Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 4.5 Bathrooms
  • Code: Bonnie Breeze
View Rental
Starting at (USD)

$1,010.00

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

$1,000.00

Captain`s Cove
St. Michaels
  • 10 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Captains Cove
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Starting at (USD)

$650.00

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

$509.00

Clearview | Save 15% on June Weeks!
Tilghman Island
  • 7 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Clearview
  • Pets Allowed
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Centreville
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Creek Cottage
  • Pets Allowed
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Starting at (USD)

$1,125.00

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

$480.00

Easton Hideaway
Easton
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Easton Hideaway
  • Pets Allowed
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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
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Starting at (USD)

$575.00

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

$760.00

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

$1,300.00

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

$670.00

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

$756.00

Loblolly Cove
Bozman-Neavitt
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Loblolly Cove
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Starting at (USD)

$700.00

Lovely Cove Farm | 15% off June Weeks
Chestertown
  • 10 Guests
  • 4 Bedrooms
  • 2.5 Bathrooms
  • Code: Lovely Cove Farm
  • Pets Allowed
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Starting at (USD)

$620.00

Mallard`s Landing
Easton
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Mallards Landing
  • Pets Allowed
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Starting at (USD)

$915.00

Off the Grid
Oxford
  • 12 Guests
  • 5 Bedrooms
  • 4.5 Bathrooms
  • Code: Off the Grid
View Rental
Starting at (USD)

$567.00

Osprey Point
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 3.5 Bathrooms
  • Code: Osprey Point
  • Pets Allowed
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Starting at (USD)

$400.00

Oxbow Farm
Chestertown
  • 11 Guests
  • 5 Bedrooms
  • 4 Bathrooms
  • Code: Oxbow Farm
  • Pets Allowed
View Rental
Starting at (USD)

$570.00

PennyWhistle - St. Michaels MD
St. Michaels
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: PennyWhistle
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Starting at (USD)

$665.00

Pines at Barrett Cove
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Pines at Barrett Cove
  • Pets Allowed
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Starting at (USD)

$583.00

Sunrise Cove
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 3 Bathrooms
  • Code: Sunrise Cove
  • Pets Allowed
View Rental