The Islands Advisors - Vacation Rentals in Shadyside Park

Waterfront Home near Annapolis, MD From US $1,805
         

10.0 (33 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Grandma's Summer House Beverly Beach From US $178
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Waterfront Home on the Chesapeake Bay! From US $618
         

10.0 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Bay House From US $150
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Round House - Panoramic Views - Chesapeake Bay From US $492
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Waterfront Sanctuary only 50 Min. From DC/Balt. From US $726
         

Waterfront Unit | Dock, Kayaks & SUPs Included From US $248
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Sunset Cottage - West River Access and Views! From US $487
         

Lovely bay views with kayaks, bikes, fire pit, crabbing & more From US $426
         

Adorable waterside cottage with pool Beach community From US $456
         

9.2 (45 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Steps to Chesapeake Bay! 'Callaway Drive Retreat' From US $223
         

9.0 (6 Reviews)
House
  • TV
  • Balcony/Terrace
  • Security/Safety
Enchanting West River Retreat From US $523
         

10.0 (9 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Zen Sunset Retreat on Waterfront at West River, MD From US $749
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Water views from every window of unique round house From US $767
         

Waterfront Shady Side Home w/Chesapeake Bay View! From US $256
         

Home w/Beach Access Boat Slip Basketball Court From US $740
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Pro Tip: Theislandsadvisors makes it easy to compare the best listings on Theislandsadvisors homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Theislandsadvisors homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shadyside Park.

Weather in Shadyside Park

View the weather forecast for Shadyside Park before booking your Shadyside Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Shadyside Park Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Shadyside Park?
How many vacation rentals are available in Shadyside Park?

Currently, the total number of properties listed in 2026 is over 50 in the Shadyside Park area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Shadyside Park.