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Huge Beach Bungalow- Yard, Beach Pass, King Beds

North Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$635

Great rentals within 20 miles that match your search

The Heart of Historic Cool in Annapolis

Annapolis house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,154

The Legends Getaway

Bryantown house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$606

Quiet Home Close to Downtown Annapolis and Parks

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$403

Gourmet Kitchen, Family and Pet Friendly Residence!

Mayo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$404

TRUE ST MICHAELS 6 ACRE WATERFRONT

St. Michaels house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 38 minutes

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Price per night from

$2,308

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,308

CHESAPEAKE MANSION - NEW POOL/12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sherwood house

  • 8 bedrooms
  • 10 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

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Price per night from

$2,885

Cozy Cedar Cottage near the Chesapeake Bay

Saint Leonard house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$150

Belle By the Bay

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$370

Beautiful Waterfront Home, Private Pool and Water Amenities- Sleeps 16

Cambridge house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 18

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Price per night from

$866

Captain Quarters - Eastport!

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$576

The Fritz

Edgewater house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,558

New, Book Me! Riverview Retreat on Warehouse Creek

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$318

Fisher House - Downtown Annapolis!

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$687

Edgewater/Mayo Getaway!

Edgewater house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$461

Charming Charles Retreat

Annapolis house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$431

Ann House Getaway

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$443

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

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

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Price per night from

$1,897

SeaGlass House by-the-Bay

Annapolis house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$673

Blue Pearl - Life on the River! Luxury estate with jacuzzi and private pier!

Broomes Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$401

Charming Annapolis Waterview home

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$804

Quiet Cottage, Hot Tub, Bay View, Block to Beach, 1hr to DC

Saint Leonard house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$252

Chesapeake Bay Getaway™ | Waterfront Experience with Pier!

Edgewater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$575

Indoor pool and spa located in beautiful Southern Maryland woodlands

Chesapeake Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,109

Breathtaking Waterfront Cambridge Getaway

Cambridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$684

West Annapolis Cottage

Annapolis house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$920

The Carrollton Cottage House

Annapolis house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$253

St. Michael's Premier in Town Summer Cottage now with private pool!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$716

Location Location! St Michaels-- In Town Cottage!

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$352

Beautiful Murray Hill Home (Annapolis)

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Comfortable and secure in a great home - almost as good as at ho” The house is set is a terrific neighborhood of annapolis within easy walking distance to two small parks on the water and to town. We all found the house a delight - the design, decorating, furnishings are tasteful and match the age and the imagery of the house. It is well equipped with comfortable bedrooms, adequate bathrooms and linens, utensils and staple supplies. We certainly will attempt to stay at this house again if we ever return to annapolis.

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Price per night from

$487

Vintage Bungalow-cozy, walk to shops, water, free pkg.

Annapolis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$476

Waterfront Property, Kayaks, Private Dock, Near Town

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$859

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

Kent Island house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$1,947

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

Chester house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,947

Still Available for 2024 Commissioning Week! Historic gem steps to USNA

Annapolis house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$465

Free Parking at Randall House in Downtown Annapolis

Annapolis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

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Price per night from

$729

Steps to Gate 1 and Free Parking at Naval-Academy Themed Home

Annapolis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

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Price per night from

$610

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