Shady Side Vacation Rentals, Houses & More


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1 / 24

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

  • 2
  • 5
  • Min stay varies

$185

Details

Great rentals within 30 miles that match your search

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1 / 24

Relaxing, Fun, Dog-Friendly Waterfront Cottage

  • 3
  • 8
  • Min stay varies

$169

Details

1 / 20

Artist Home/studio 1 block from Chesapeake Bay

  • 2
  • 6
  • 2 nights min

$200

Details

1 / 26

Annapolis Crows Nest Cottage: Chesapeake Bay View

  • 5
  • 20
  • 2 nights min

$695

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

1 / 11

Panoramic Views of Herrington Harbour on the Bay.

  • 3
  • 8
  • 1 night min

$450

Details

1 / 14

Luxury Waterfront Apartment in Gated Resort Marina

  • 3
  • 12
  • 2 nights min

$625

Details

1
1 / 36

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

  • 3
  • 8
  • Min stay varies

$400

Details

1 / 9

Renovated Luxury Waterview House

  • 3
  • 6
  • 2 nights min

$250

Details

1 / 27

New! Waterfront 5BR Stevensville House w/ Pier!

  • 5
  • 12
  • Min stay varies

$375

Details

1 / 5

Annapolis Bay Charters Luxury Yacht Charters

  • 4
  • 10
  • 2 nights min

$1250

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

5
1 / 17

Seahorse Guest Cottage near the Bay, dog friendly

  • 1
  • 5
  • 2 nights min

$150

Details

1 / 23

Charming Eastport Home

  • 3
  • 8
  • 5 nights min

$300

Details

1 / 16

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

  • 1
  • 4
  • 2 nights min

$175

Details

1 / 4

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

  • 2
  • 5
  • 3 nights min

$250

Details

1 / 15

Location,location,location,walk to city dock,free

  • 2
  • 5
  • Min stay varies

$180

Details

1 / 24

Charming Artists Home in Eastport/Annapolis

  • 3
  • 6
  • 3 nights min

$375

Details

3
1 / 30

Beautiful Murray Hill Home (Annapolis)

  • 4
  • 9
  • Min stay varies

$425

Details

1 / 17

Excellent Location in Downtown Annapolis- walk to everything !

  • 3
  • 7
  • 2 nights min

$299

Details

3
1 / 24

Charming and Spacious Annapolis Victorian

  • 6
  • 12
  • Min stay varies

$750

Details

2
1 / 29

Charming Home close to historic district

  • 2
  • 6
  • 2 nights min

$250

Details

1
1 / 7

Charming Townhouse - Steps to City Dock and USNA

  • 3
  • 8
  • 3 nights min

$450

Details

1 / 18

Family home one minute work away from Navy Stadium

  • 3
  • 6
  • 5 nights min

$550

Details

17
1 / 25

*BOOK NOW* Beautiful Cottage in historic Annapolis

  • 3
  • 6
  • 2 nights min

$350

Details

3
1 / 17

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

  • 4
  • 10
  • Min stay varies

$425

Details

1 / 26

Stunning Home in Historic District Annapolis, Steps to Academy

  • 4
  • 9
  • Min stay varies

$900

Details

1 / 24

Perfect Annapolis with Lots of Parking & Hot Tub

  • 4
  • 10
  • 2 nights min

$495

Details

1 / 7

2. Private 20 acre waterfront estate - studio apt

  • 1
  • 2
  • 1 night min

$300

Details

1
1 / 24

Amazing Waterfront Annapolis & easy walk downtown

  • 4
  • 14
  • 2 nights min

$850

Details

2
1 / 6

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

  • 2
  • 4
  • 2 nights min

$179

Details

3
1 / 35

Comfortable, Spacious & Fun! 6 Acres Pool & Shore

  • 5
  • 10
  • 3 nights min

$1000

Details

1 / 10

Condo Laval/Montreal 3mths or L/T: Pool,Tennis,Gym

  • 2
  • 4
  • 90 nights min

$60

Details

1 / 14

Halos'Haven Vacation Rental

  • 5
  • 10
  • 2 nights min

$700

Details

1
1 / 19

Annapolis Waterfront very near USNA

  • 3
  • 6
  • Min stay varies

$285

Details

5
1 / 11

ENDLESS SUNSETS - The perfect getaway!

  • 3
  • 8
  • Min stay varies

$275

Details

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