View All Properties

Feel free to browse our great selection of cottages, waterfront homes and estates. We would be happy to help you find just the right spot for your vacation! 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)

$360.00

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

$1,024.00

Blue Gates
Easton
  • 10 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Blue Gates
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Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 4.5 Bathrooms
  • Code: Bonnie Breeze
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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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Starting at (USD)

$557.00

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

$529.00

Captain`s Cottage
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)

$323.00

Caulk`s Cove
Bozman-Neavitt
  • 8 Guests
  • 3 Bedrooms
  • 2.5 Bathrooms
  • Code: Caulks Cove
  • Pets Allowed
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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)

$455.00

Chesapeake Pines
Royal Oak
  • 8 Guests
  • 4 Bedrooms
  • 4 Bathrooms
  • Code: Chesapeake Pines
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Starting at (USD)

$509.00

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

$460.00

Crabber`s Cove
St. Michaels
  • 6 Guests
  • 3 Bedrooms
  • 3 Bathrooms
  • Code: Crabbers Cove
  • 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)

$185.00

Dukes Street Cottage
Easton
  • 4 Guests
  • 2 Bedrooms
  • 2 Bathrooms
  • Code: Dukes Street Cottage
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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
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)

$285.00

Graceful View
Bozman-Neavitt
  • 6 Guests
  • 3 Bedrooms
  • 2 Bathrooms
  • Code: Graceful View
  • 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)

$615.00

Holland Point Preserve
Cambridge
  • 14 Guests
  • 5 Bedrooms
  • 5 Bathrooms
  • Code: Holland Point Preserve
  • 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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