Shady Side, MD, USA Vacation Rentals

United States Maryland Tracys Landing vacation rental compare prices direct by owner 40836232

LUXE Waterfront Retreat w Pool, Hot Tub, Game Den

5.0 (10)

5 Bedrooms • 14 Guests

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United States Maryland Edgewater vacation rental compare prices direct by owner 23633820

Coastal Edgewater Home w/ Private Hot Tub!

4.5 (72)

5 Bedrooms • 9 Guests

$456 avg/night

United States Maryland Edgewater vacation rental compare prices direct by owner 36850230

Edgewater's Shelby on the Bay

4.9 (36)

4 Bedrooms • 10 Guests

Available on

United States Maryland Shady Side vacation rental compare prices direct by owner 44253483

Steps to Chesapeake Bay! 'Callaway Drive Retreat'

4.7 (32)

3 Bedrooms • 6 Guests

$302 avg/night

United States Maryland Edgewater vacation rental compare prices direct by owner 43065572

Chesapeake Bay Views w Deck, Parking, Beach Access

4.6 (10)

3 Bedrooms • 11 Guests

Available on

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United States Maryland Deale vacation rental compare prices direct by owner 44400077

Modern Waterfront Home w/ Dock & Views in Deale

4.5 (1)

4 Bedrooms • 10 Guests

Available on

United States Maryland Deale vacation rental compare prices direct by owner 37985068

Water-View Deale Home: Walk to Marina, Restaurants

5.0 (2)

5 Bedrooms • 13 Guests

$761 avg/night

United States Maryland Edgewater vacation rental compare prices direct by owner 25175788

Searenity Stays, a Cozy Home

4.9 (84)

3 Bedrooms • 6 Guests

$315 avg/night

United States Maryland Deale vacation rental compare prices direct by owner 11581581

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

4.9 (647)

2 Bedrooms • 4 Guests

Available on

United States Maryland Deale vacation rental compare prices direct by owner 23679662

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

4.9 (110)

4 Bedrooms • 9 Guests

Available on

United States Maryland Deale vacation rental compare prices direct by owner 361814

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

4.8 (203)

3 Bedrooms • 8 Guests

$304 avg/night

United States Maryland Deale vacation rental compare prices direct by owner 29193357

Waterfront, Beautiful Cozy & comfy private room

5.0 (5)

3 Bedrooms • 2 Guests

Available on

United States Maryland Shady Side vacation rental compare prices direct by owner 11829834

Iconic Chesapeake. Unparalleled Luxury.

5.0 (218)

3 Bedrooms • 5 Guests

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United States Maryland Deale vacation rental compare prices direct by owner 26629425

Beautiful Waterfront Escape w/ Gorgeous Views

5.0 (76)

4 Bedrooms • 8 Guests

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United States Maryland Shady Side vacation rental compare prices direct by owner 27513738

Peaceful Waterfront Getaway

5.0 (74)

6 Bedrooms • 13 Guests

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United States Maryland Deale vacation rental compare prices direct by owner 11462891

Chesapeake Bay Cottage

5.0 (279)

3 Bedrooms • 7 Guests

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United States Maryland Deale vacation rental compare prices direct by owner 211942

Million Dollar View

4.9 (213)

4 Bedrooms • 8 Guests

Available on

United States Maryland Deale vacation rental compare prices direct by owner 23690542

Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt

4.9 (54)

6 Bedrooms • 13 Guests

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United States Maryland Tracys Landing vacation rental compare prices direct by owner 11451655

The Driftwood Lodge - Chesapeake Bay Waterfront

4.8 (102)

5 Bedrooms • 14 Guests

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United States Maryland Harwood vacation rental compare prices direct by owner 36689015

Pool & Yard Retreat | 4BR | 20 Min to Annapolis

4.8 (39)

4 Bedrooms • 12 Guests

$932 avg/night

United States Maryland Shady Side vacation rental compare prices direct by owner 29057104

Baydream Believer -Chesapeake Bay water community

4.8 (91)

3 Bedrooms • 8 Guests

Available on

United States Maryland Shady Side vacation rental compare prices direct by owner 15576969

Waterfront Sanctuary only 50 Min. From DC/Balt.

5.0 (5)

5 Bedrooms • 12 Guests

Available on

United States Maryland Deale vacation rental compare prices direct by owner 26599383

Modern Bay Dream

5.0 (22)

3 Bedrooms • 10 Guests

Available on

United States Maryland Edgewater vacation rental compare prices direct by owner 34832181

Holly Hill Haven

5.0 (6)

3 Bedrooms • 10 Guests

$666 avg/night

United States Maryland Lothian vacation rental compare prices direct by owner 40459383

Modern Farmhouse | 12.5 Acres & 2 Fire Pits

5.0 (25)

5 Bedrooms • 10 Guests

$452 avg/night

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