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291 houses

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Beautiful Luxury Estate Home

Darnestown house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,317

Kingsbay 'Bayhouse' Vacation Rental

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,140

Kingsbay Waterside Retreat Compound

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,369

Kingsbay Mansion

Marion Station house

  • 5 bedrooms
  • 13 bathrooms
  • sleeps 21

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$2,863

Quiet House on Cul de Sac

Rockville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$401

KENT ISLAND-OCEAN VIEW Home for rent-4 bedrooms EASTERN SHORE sleeps 10-12

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,947

Grove Guest Home

Frederick house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$218

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Tracys Landing house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$727

Waterfront pier, putting green just minutes from downtown Annapolis

Riva house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$725

Kingsbay Dockside

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,088

Pool and Bay Views on wrap around deck in Kent Island

Stevensville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$321

Luxury Pool House w/ Sun & Game Rooms near MGM/National Harbor

Fort Washington house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$574

Ship's Cove Inn and Resort in St. Michaels, MD

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,890

Luxury Waterfront home with private pier and guest house

Annapolis house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$907

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$200

Private pier and pool at this waterfront Chestertown home

Chestertown house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$413

DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-12

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$1,947

The Annapolis General House

Parole house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Rental types Private outdoor pool (unheated)

All filters match

Price per night from

$690

These homes match some but not all of your filters. Clear all filters

Waterfront Getaway - View of bay from your bed

Romancoke studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$230

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$181

Downtown Suite with Water Views & Balcony Access from every room!

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$228

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$102

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$198

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$258

The magnificant Gateway Grand

Ocean City condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$786

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,117

Luxury Getaway A Condo at Sunset Island Ocean City

Ocean City apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$218

Great deal 4 Bedroom House Near the Ferry Park

Rock Hall house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$277

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$403

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$289

Spacious Studio 3 Mins Inner Harbor

Baltimore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$168

Charming town home near Wash DC/Dwtn Silver Spring

White Oak house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$150

Renovated Townhome w/ King Bed & Perfect Location!

Baltimore house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$254

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$404

BEST Deal in the DC Area! Cute and Comfy Bed n Breakfast Near EVERYthing!

Suitland house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$341

1920s Restored Home|10 mins to main attractions

Baltimore house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 6 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$231

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$2,308

1 of 2 match: Private outdoor pool (unheated), Rental types

1 of 2 filters match

Price per night from

$543

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