Updating...

Enter dates for more accurate prices

Shady Side Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Shady Side Rentals

10 Houses

Renovated Luxury Waterview House

North Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$300

1 / 9

Charming Annapolis home with stunning water views

Annapolis house

4 bedrooms / 4 bathrooms / sleeps 11

Price per night from

$500

1 / 55

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

Tilghman cottage

3 bedrooms / 2 bathrooms / sleeps 6

“We loved it!” We had a great (albeit too short!) family getaway at the Roost! The cottage is extremely clean, comfortable, well-maintained, and spacious. The kids (ages 6 and 20 months) loved it -- especially the bunk beds and the nice backyard, and t

Price per night from

$200

1 / 20

The Yellow House- Gorgeous Southern Colonial

Annapolis house

6 bedrooms / 6 bathrooms / sleeps 14

Responds fast! avg. 1 hour 35 minutes

Price per night from

$990

1 / 43

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

Price per night from

$695

1 / 26

Seahorse Guest Cottage near the Bay, dog friendly

North Beach cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 12 minutes

Price per night from

$160

1 / 17

Panoramic Views of Herrington Harbour on the Bay.

North Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$500

1 / 11

Luxury Boat & Bed 78' Motor Yacht "Laid Off"

Edgewater yacht

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$989

1 / 4

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

Kent Island house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$525

1 / 17

Kent Island Beach House II:Chesapeake Bay Fisherman's Village at Kentmorr Marina

Stevensville house

4 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$545

1 / 9
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more