Shady Side Rentals By Owner

There are a lot of options in Shady Side. If you plan on staying in the Shady Side area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Shady Side:

• Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
• Charming WATERFRONT 3BR/2BA cottage on Chesapeake Bay - 30 mins from Annapolis
• Chesapeake Bay House
• Bay Front Manor House
• The Bay House
• Spacious Luxury 6 BR Home, Sleeps 16, Private Pool, In Nature, Convenient to DC
• 5-years young STUNNING home with water view!
• River Cottage with Beach and Dock
• Water views from every window of unique round house
• Waterfront Shady Side Home w/Chesapeake Bay View!

There are many large, family-friendly vacation homes available in Shady Side; however, here are the most popular family rentals listed on our site:

• Waterfront Home near Annapolis, MD
• Grandma's Summer House Beverly Beach
• Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
• Steps to Chesapeake Bay! Callaway Drive Retreat

Yes, there are 57 self-catering vacation homes in Shady Side that have hot tubs, swimming pools, & other amenities.

There are more than 57 luxury villas and vacation homes in or near Shady Side. Filter by price to compare find the most expensive places to stay on Bespokeusatravel.

Yes, there are 57 pet friendly vacation homes and places to stays that are available in or near Shady Side that you may consider.