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1 / 14

Halos'Haven Vacation Rental

  • 5
  • 10
  • 2 nights min

$701

Details

Great rentals within 20 miles that match your search

1 / 18

St. Michaels Waterfront Home W/Dock for 2 boats

  • 2
  • 5
  • Min stay varies

$250

Details

1 / 12

Love Point Bay Luxury Waterfront House

  • 3
  • 10
  • 3 nights min

$900

Details

1 / 9

Renovated Luxury Waterview House

  • 3
  • 6
  • 2 nights min

$250

Details

1 / 55

Waterfront Vacation Home with Private Beach

  • 3
  • 6
  • 2 nights min

$331

Details

1 / 11

Panoramic Views of Herrington Harbour on the Bay.

  • 3
  • 8
  • 1 night min

$450

Details

1 / 17

KI Golf House-A PAR for the Course & Mile to Beach

  • 4
  • 10
  • Min stay varies

$387

Details

1 / 35

Luxury vacation condominum with private beach

  • 4
  • 10
  • 2 nights min

$440

Details

1 / 14

Luxury Waterfront Apartment in Gated Resort Marina

  • 3
  • 12
  • 2 nights min

$625

Details

1 / 24

Charming and Spacious Annapolis Victorian

  • 6
  • 12
  • Min stay varies

$750

Details

1 / 7

St. Michael's Premier in Town Summer Cottage!

  • 2
  • 4
  • 2 nights min

$285

Details

1 / 17

Deerpond Carriage House

  • 1
  • 2
  • 3 nights min

$181

Details

1 / 26

Annapolis Crows Nest Cottage: Chesapeake Bay View

  • 5
  • 20
  • 2 nights min

$696

Details

1 / 43

The Yellow House- Gorgeous Southern Colonial

  • 6
  • 14
  • 4 nights min

$996

Details

1 / 21

Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)

  • 4
  • 8
  • 3 nights min

$181

Details

1 / 24

Relaxing, Fun, Dog-Friendly Waterfront Cottage

  • 3
  • 8
  • Min stay varies

$170

Details

1 / 15

BACK STREET RETREAT

  • 3
  • 6
  • Min stay varies

$343

Details

1 / 8

Charming Coastal Cottage Minutes to St. Michaels

  • 2
  • 6
  • Min stay varies

$176

Details

1 / 23

EASTERN SHORE MARYLAND WELCOMES YOU

  • 1
  • 2
  • 1 night min

$76

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1 / 39

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$300

Details

1 / 39

Cottage at Heron Cove, Chesapeake Bay, Cambridge

  • 3
  • 5
  • Min stay varies

$201

Details

1 / 4

LOCATION,LOCATION,,LUXURY,WALK TO CITY ,PARKING. Annapolis, MD

  • 2
  • 5
  • 3 nights min

$250

Details

1 / 51

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

  • 3
  • 6
  • 2 nights min

$250

Details

1 / 23

Charming Eastport Home

  • 3
  • 8
  • 5 nights min

$300

Details

1 / 30

Beautiful Murray Hill Home (Annapolis)

  • 4
  • 9
  • Min stay varies

$425

Details

1 / 34

Private Beach, Waterfront Room Rentals 1

  • 1
  • 2
  • 2 nights min

$130

Details

1 / 29

Charming Home close to historic district

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 34

Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$902

Details

1 / 10

C/ean & Cozy

  • 1
  • 2
  • 1 night min

$59

Details

1 / 22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$376

Details

1 / 20

Love Point Waterfront

  • 3
  • 12
  • 3 nights min

$201

Details

1 / 44

Private Beach, Waterfront Room Rentals 3

  • 1
  • 2
  • 2 nights min

$100

Details

1 / 25

*BOOK NOW* Beautiful Cottage in historic Annapolis

  • 3
  • 6
  • 2 nights min

$351

Details

1 / 16

Neat & Clean 1BR Apartment in Historic Annapolis w/Wifi - Prime Location

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 20

IRONMAN AND 5KERS

  • 1
  • 2
  • 1 night min

$88

Details

1 / 27

Location Location! St Michaels-- In Town Cottage!

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 20

Artist Home/studio 1 block from Chesapeake Bay

  • 2
  • 6
  • 2 nights min

$201

Details

1 / 7

Charming Townhouse - Steps to City Dock and USNA

  • 3
  • 8
  • 3 nights min

$450

Details

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