Shady Side Vacation Rentals, Houses & More


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Areas near Shady Side

1 / 24

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

  • 2
  • 5
  • Min stay varies

$186

Details

Great rentals within 20 miles that match your search

1 / 30

Beautiful Murray Hill Home (Annapolis)

  • 4
  • 9
  • Min stay varies

$425

Details

1 / 29

Charming Home close to historic district

  • 2
  • 6
  • 2 nights min

$251

Details

1 / 16

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

  • 1
  • 4
  • 2 nights min

$175

Details

1 / 26

Stunning Home in Historic District Annapolis, Steps to Academy

  • 4
  • 9
  • Min stay varies

$901

Details

1 / 17

Excellent Location in Downtown Annapolis- walk to everything !

  • 3
  • 7
  • 2 nights min

$299

Details

1 / 19

Clean & Spacious

  • 4
  • 9
  • 1 night min

$351

Details

1 / 19

Annapolis Waterfront very near USNA

  • 3
  • 6
  • Min stay varies

$286

Details

1 / 7

Charming Townhouse - Steps to City Dock and USNA

  • 3
  • 8
  • 3 nights min

$451

Details

1 / 18

Family home one minute work away from Navy Stadium

  • 3
  • 6
  • 5 nights min

$551

Details

1 / 21

Annapolis Area Waterfront Home

  • 5
  • 11
  • Min stay varies

$551

Details

1 / 24

Charming and Spacious Annapolis Victorian

  • 6
  • 12
  • Min stay varies

$750

Details

1 / 6

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

  • 1
  • 6
  • 2 nights min

$230

Details

1 / 11

ENDLESS SUNSETS - The perfect getaway!

  • 3
  • 8
  • Min stay varies

Inquire for Rates

Details

1 / 20

Artist Home/studio 1 block from Chesapeake Bay

  • 2
  • 6
  • 2 nights min

$200

Details

1 / 9

Renovated Luxury Waterview House

  • 3
  • 6
  • 2 nights min

$251

Details

1 / 39

Love Point Bay Vacation Home

  • 2
  • 6
  • 2 nights min

$299

Details

1 / 33

Upscale House/12 MINUTES FROM DC

  • 5
  • 16
  • 3 nights min

$490

Details

1 / 20

CHILD/FAMILY FRIENDLY HOME

  • 5
  • 16
  • 3 nights min

$400

Details

1 / 8

Charming Coastal Cottage Minutes to St. Michaels

  • 2
  • 6
  • Min stay varies

$175

Details

1 / 24

Perfect Annapolis with Lots of Parking & Hot Tub

  • 4
  • 10
  • 2 nights min

$495

Details

1 / 22

Sandy Pines: Enjoy Harris Creek w/Pool and Boats

  • 4
  • 10
  • Min stay varies

$376

Details

1 / 6

Spacious, Modern Condo nr. Navy Stadium, downtown & Mall . Easy access route 50

  • 2
  • 4
  • 2 nights min

$179

Details

1 / 21

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

  • 4
  • 8
  • 3 nights min

$181

Details

1 / 34

Grandview at Pleasure Point

  • 8
  • 27
  • 7 nights min

$902

Details

1 / 25

*BOOK NOW* Beautiful Cottage in historic Annapolis

  • 3
  • 6
  • 2 nights min

$351

Details

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 / 7

The Peaceful Palace

  • 1
  • 2
  • 1 night min

$26

Details

1 / 9

The Peaceful Palace Room 2

  • 1
  • 2
  • 1 night min

$26

Details

1 / 10

C/ean & Cozy

  • 1
  • 2
  • 1 night min

$60

Details

1 / 18

St. Michaels Waterfront Home W/Dock for 2 boats

  • 2
  • 5
  • Min stay varies

$251

Details

1 / 20

Love Point Waterfront

  • 3
  • 12
  • 3 nights min

$200

Details

1 / 7

St. Michael's Premier in Town Summer Cottage!

  • 2
  • 4
  • 2 nights min

$286

Details

1 / 51

Walk to Shops/Eateries Charming Cottage. Dogs Wel.

  • 3
  • 6
  • 2 nights min

$251

Details

1 / 14

Washington Beltway Resort

  • 4
  • 10
  • 3 nights min

$200

Details

1 / 27

Location Location! St Michaels-- In Town Cottage!

  • 2
  • 5
  • Min stay varies

$195

Details

1 / 20

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

  • 3
  • 6
  • 3 nights min

$200

Details

1 / 12

Great Family House, good for touring DC & MD

  • 4
  • 10
  • 2 nights min

$195

Details

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