FROM $3050
Swan's Rest
Easton
Beds: 3 | Baths: 3 | Sleeps: 6
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FROM $4000
The Landing
Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $3800
The Bay House on Easy Lane
Centreville
Beds: 3 | Baths: 3.5 | Sleeps: 8
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FROM $3000
Escape Farm
Royal Oak
Beds: 3 | Baths: 4 | Sleeps: 6
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FROM $1890
Caulk's Cove
Bozman
Beds: 3 | Baths: 2.5 | Sleeps: 6
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FROM $6370
Blue Gates
Easton
Beds: 4 | Baths: 4 | Sleeps: 10
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FROM $8500
Acorn Point
Easton
Beds: 5 | Baths: 5.5 | Sleeps: 10
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FROM $4900
Town and Country
Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 10
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FROM $1200
Duck Cove
Neavitt
Beds: 2 | Baths: 1 | Sleeps: 4
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FROM $7000
Bayberry Cove
Cambridge
Beds: 7 | Baths: 5.5 | Sleeps: 17
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FROM $2720
Pines at Irish Creek
Royal Oak
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $4500
- $6000
Thornton
Chestertown
Beds: 6 | Baths: 4.5 | Sleeps: 11
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FROM $1500
Simplicity Cottage
Tilghman
Beds: 2 | Baths: 1.5 | Sleeps: 4
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FROM $4500
At Tricefields Court
Saint Michaels
Beds: 4 | Baths: 5 | Sleeps: 8
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FROM $2400
- $2750
Crabber's Cove
St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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FROM $2850
Clearview
Tilghman
Beds: 3 | Baths: 3 | Sleeps: 6
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FROM $1250
Memory Lane
Oxford
Beds: 4 | Baths: 2full, 2 half | Sleeps: 8
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FROM $2050
Mallard Point Cottage
McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $2135
Bay Water Cottage
Church Creek
Beds: 4 | Baths: 3.5 | Sleeps: 8
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FROM $5625
Captain's Cove
Saint Michaels
Beds: 5 | Baths: 4.5 | Sleeps: 10
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FROM $4250
Heron Point
Royal Oak
Beds: 4 | Baths: 2.5 | Sleeps: 8
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FROM $2889
- $8500
McKendree Street Mainland
Annapolis
Beds: 4 | Baths: 3 | Sleeps: 10
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FROM $4075
Loblolly Cove
Neavitt
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $3225
Osprey Point
Saint Michaels
Beds: 4 | Baths: 3.5 | Sleeps: 8
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FROM $5250
Lee Haven
Easton
Beds: 5 | Baths: 4.5 | Sleeps: 10
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FROM $5800
Ben Oaks Drive
Severna Park
Beds: 4 | Baths: 2.5 | Sleeps: 10
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FROM $4025
Pines at Barrett Cove
Saint Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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FROM $4600
Judith's Garden
Oxford
Beds: 4 | Baths: 2.5 | Sleeps: 8
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FROM $2850
Tidal Serenity
Taylors Island
Beds: 5 | Baths: 2.5 | Sleeps: 15
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FROM $4750
Mill Creek
Wye Mills
Beds: 5 | Baths: 3.5 | Sleeps: 10
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FROM $3000
Sunrise Cove
Saint Michaels
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $3450
Cedar Cove on the Miles
Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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FROM $3500
Bushey Heath Farm
Royal Oak
Beds: 4 | Baths: 2 | Sleeps: 8
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FROM $4165
Holland Point Preserve
Taylors Island
Beds: 5 | Baths: 5 | Sleeps: 14
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FROM $6500
Hudson Manor
Cambridge
Beds: 7 | Baths: 6 | Sleeps: 22
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FROM $1750
Carpenter Alley Cottage
St. Michaels
Beds: 3 | Baths: 3 | Sleeps: 6
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FROM $5250
- $7750
Willoughby
Cambridge
Beds: 7 | Baths: 6 | Sleeps: 24
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FROM $5800
Broadwater View
Royal Oak
Beds: 5 | Baths: 4.5 | Sleeps: 10
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FROM $1050
- $2750
East Street Easy Walk
Annapolis
Beds: 1 | Baths: 1.5 | Sleeps: 3
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FROM $3500
- $4200
The Water House
Easton
Beds: 5 | Baths: 5.5 | Sleeps: 9
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FROM $12500
Fairview
Easton
Beds: 5 | Baths: 6 | Sleeps: 10
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FROM $5850
Sycamore Acres
Easton
Beds: 6 | Baths: 5.5 | Sleeps: 12
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FROM $1500
Pride and Joy
Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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FROM $1250
Sunflower Cottage
Oxford
Beds: 2 | Baths: 1 | Sleeps: 4
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FROM $2793
- $14000
22 Fleet Street
Annapolis
Beds: 3 | Baths: 2.5 | Sleeps: 6
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FROM $2750
PennyWhistle
McDaniel
Beds: 4 | Baths: 3 | Sleeps: 8
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FROM $2100
Chesapeake Pines
Easton
Beds: 4 | Baths: 4 | Sleeps: 8
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FROM $1850
Oxford Beach Cottage
Oxford
Beds: 3 | Baths: 2 | Sleeps: 6
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FROM $2450
Graceful View
Bozman
Beds: 3 | Baths: 2 | Sleeps: 6
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FROM $11000
Retreat on Grace Creek
Bozman
Beds: 6 | Baths: 8 | Sleeps: 12
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FROM $4500
Emily's Lane
Wittman
Beds: 4 | Baths: 3.5 | Sleeps: 10
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FROM $4750
Creek Cottage
Centreville
Beds: 4 | Baths: 4 | Sleeps: 10
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FROM $4900
Oxford Oasis
Oxford
Beds: 6 | Baths: 7 | Sleeps: 12
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FROM $3500
Indian Fields
Cambridge
Beds: 5 | Baths: 4.5 | Sleeps: 13
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FROM $11900
Belle Aire Landing
East New Market
Beds: 9 | Baths: 6 | Sleeps: 22
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FROM $3940
- $10500
Nantucket on the Chesapeake
Annapolis
Beds: 4 | Baths: 3.5 | Sleeps: 10
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FROM $2889
- $8500
FROM $3940
- $10500