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Areas near North Beach

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1 / 9

Renovated Luxury Waterview House

  • 3
  • 6
  • 2 nights min

$250

Details

5
1 / 17

Seahorse Guest Cottage near the Bay, dog friendly

  • 1
  • 5
  • 2 nights min

$150

Details

1 / 11

Panoramic Views of Herrington Harbour on the Bay.

  • 3
  • 8
  • 1 night min

$450

Details

Great rentals within 30 miles that match your search

1 / 20

Artist Home/studio 1 block from Chesapeake Bay

  • 2
  • 6
  • 2 nights min

$200

Details

1
1 / 24

Relaxing, Fun, Dog-Friendly Waterfront Cottage

  • 3
  • 8
  • Min stay varies

$169

Details

1
1 / 20

Chesapeake camping. 40 miles to Wash DC. 1 mile to river. 10 miles to beaches.

  • 2
  • 6
  • 1 night min

$96

Details

1 / 24

NEW! 2BR Shady Side House on the Chesapeake Bay!

  • 2
  • 5
  • Min stay varies

$185

Details

6
1 / 20

Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge

  • 3
  • 6
  • 3 nights min

$200

Details

1 / 24

Magical Bayfront Home

  • 3
  • 8
  • 7 nights min

$414

Details

4
1 / 22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$375

Details

10
1 / 34

Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$901

Details

1
1 / 18

St. Michaels Waterfront Home W/Dock for 2 boats

  • 2
  • 5
  • Min stay varies

$250

Details

1
1 / 36

Impressive 3BR Stevensville House Overlooking Eastern Shore w/Wifi, Private

  • 3
  • 8
  • Min stay varies

$400

Details

3
1 / 35

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

  • 5
  • 10
  • 3 nights min

$1000

Details

1 / 8

Charming Coastal Cottage Minutes to St. Michaels

  • 2
  • 6
  • Min stay varies

$175

Details

1 / 14

Halos'Haven Vacation Rental

  • 5
  • 10
  • 2 nights min

$700

Details

1 / 26

Annapolis Crows Nest Cottage: Chesapeake Bay View

  • 5
  • 20
  • 2 nights min

$696

Details

1 / 27

New! Waterfront 5BR Stevensville House w/ Pier!

  • 5
  • 12
  • Min stay varies

$375

Details

1
1 / 26

Peaceful 3BR Annapolis House on Oyster Creek w/ Amazing Views of the Chesapeake Bay

  • 3
  • 9
  • 2 nights min

$350

Details

1 / 43

The Yellow House- Gorgeous Southern Colonial

  • 6
  • 14
  • 4 nights min

$995

Details

5
1 / 11

ENDLESS SUNSETS - The perfect getaway!

  • 3
  • 8
  • Min stay varies

$275

Details

1 / 6

Halo's Haven Guest Quarters

  • 3
  • 6
  • 2 nights min

$325

Details

1 / 14

Luxury Waterfront Apartment in Gated Resort Marina

  • 3
  • 12
  • 2 nights min

$625

Details

1 / 10

Harbor Cottage at the Chesapeake Bay

  • 2
  • 6
  • 3 nights min

$260

Details

1 / 17

The "SWEET SPOT" - a special cottage on the Bay

  • 2
  • 4
  • 4 nights min

$145

Details

3
1 / 17

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

  • 4
  • 10
  • Min stay varies

$425

Details

1 / 26

New! Beachfront 4BR St. Leonard Cottage w/ Deck!

  • 4
  • 8
  • Min stay varies

$175

Details

4
1 / 23

Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!

  • 2
  • 5
  • Min stay varies

$160

Details

12
1 / 24

Premier Cottage in St. Michaels- In Town Location!

  • 2
  • 5
  • Min stay varies

$205

Details

21
1 / 27

Location Location! St Michaels-- In Town Cottage!

  • 2
  • 5
  • Min stay varies

$195

Details

3
1 / 25

Waterview Cottage In St. Michaels!

  • 2
  • 5
  • Min stay varies

$215

Details

11
1 / 30

Large Historic Thomas Harrison House on Harbor in St. Michaels Town

  • 7
  • 9
  • Min stay varies

$390

Details

1 / 38

St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds

  • 6
  • 12
  • Min stay varies

$780

Details

1 / 5

Annapolis Bay Charters Luxury Yacht Charters

  • 4
  • 10
  • 2 nights min

$1250

Details

2
1 / 6

Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX

  • 1
  • 6
  • 2 nights min

$230

Details

1
1 / 51

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

  • 3
  • 6
  • 2 nights min

$250

Details

2
1 / 15

Beautiful Eastport Home, Walk to Naval Academy

  • 3
  • 7
  • Min stay varies

$450

Details

1 / 13

Charming 1BR Saint Leonard Bungalow Overlooking Wells Cove

  • 1
  • 2
  • 2 nights min

$85

Details

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