52+ Vacation Rentals Near Shadyside Park |
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  2. Maryland
  3. Shady Side
  4. Shadyside Park

Sell Off Cruises - Vacation Rentals in Shadyside Park

Waterfront Home near Annapolis, MD From US $2,077
         

10.0 (33 Reviews)
House
Waterfront Home near Annapolis, MD
  • Air Conditioner
  • Parking
  • Pool

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Otterspace at the beach From US $153
         

10.0 (1 Review)
House
Otterspace at the beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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West River Waterfront Escape with Boat Lift, Kayaks & Bay Views From US $760
         

10.0 (32 Reviews)
House
West River Waterfront Escape with Boat Lift, Kayaks & Bay Views
  • Air Conditioner
  • Parking
  • Pet Friendly

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Steps to Chesapeake Bay! 'Callaway Drive Retreat' From US $303
         

9.6 (7 Reviews)
House
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
  • Parking
  • View
  • Ocean View

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Waterfront Sanctuary only 50 Min. From DC/Balt. From US $1,007
         

10.0 (5 Reviews)
House
Waterfront Sanctuary only 50 Min. From DC/Balt.
  • Air Conditioner
  • Parking
  • TV

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Waterfront Getaway, Dock Your Boat & Play! From US $401
         

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9.4 (5 Reviews)
House
Waterfront Getaway, Dock Your Boat & Play!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunset Cottage - West River Access and Views! From US $576
         

10.0 (5 Reviews)
House
Sunset Cottage - West River Access and Views!
  • Air Conditioner
  • Parking
  • TV

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Peaceful 2-bedroom/2-bathroom house with WiFi and AC in serene Shady Side From US $482
         

10.0 (4 Reviews)
House
Peaceful 2-bedroom/2-bathroom house with WiFi and AC in serene Shady Side
  • Air Conditioner
  • Parking
  • TV

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Waterfront Unit | Dock, Kayaks & SUPs Included From US $327
         

10.0 (3 Reviews)
House
Waterfront Unit | Dock, Kayaks & SUPs Included
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Bayfront Escape in Edgewater with Deck, Balcony, and Walk to Beach From US $940
         

10.0 (1 Review)
House
Bayfront Escape in Edgewater with Deck, Balcony, and Walk to Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lovely bay views with kayaks, bikes, fire pit, crabbing & more From US $365
         

9.6 (33 Reviews)
House
Lovely bay views with kayaks, bikes, fire pit, crabbing & more
  • Air Conditioner
  • Parking
  • Pet Friendly

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Steps to Chesapeake Bay! 'Callaway Drive Retreat' From US $327
         

9.4 (8 Reviews)
House
Steps to Chesapeake Bay! 'Callaway Drive Retreat'
  • TV
  • Balcony/Terrace
  • Security/Safety

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Luxury 5-Star Chesapeake Bay Waterfront Home From US $556
         

New
House
Luxury 5-Star Chesapeake Bay Waterfront Home
  • Air Conditioner
  • Parking
  • TV

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3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access From US $255
         

New
House
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
  • Air Conditioner
  • Parking
  • TV

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Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi From US $1,042
         

10.0 (12 Reviews)
House
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
  • Air Conditioner
  • Parking
  • Pet Friendly

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Zen Sunset Retreat on Waterfront at West River, MD From US $921
         

10.0 (7 Reviews)
House
Zen Sunset Retreat on Waterfront at West River, MD
  • Air Conditioner
  • Parking
  • TV

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Charming WATERFRONT 3BR/2BA cottage - 20 mins to Annapolis/40 mins to downtwn DC From US $459
         

10.0 (3 Reviews)
House
Charming WATERFRONT 3BR/2BA cottage - 20 mins to Annapolis/40 mins to downtwn DC
  • Air Conditioner
  • Parking
  • TV

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Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC. From US $208
         

9.8 (50 Reviews)
Cottage
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
  • Air Conditioner
  • Parking
  • TV

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Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway! From US $198
         

10.0 (33 Reviews)
Apartment
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
  • Air Conditioner
  • Parking
  • TV

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Round House - Panoramic Views - Chesapeake Bay From US $632
         

10.0 (17 Reviews)
House
Round House - Panoramic Views - Chesapeake Bay
  • Air Conditioner
  • Parking
  • TV

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Water views from every window of unique round house From US $767
         

10.0 (3 Reviews)
House
Water views from every window of unique round house
  • Air Conditioner
  • Parking
  • TV

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

10.0 (3 Reviews)
House
Waterfront Shady Side Home w/Chesapeake Bay View!
  • Air Conditioner
  • Parking
  • TV

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

10.0 (2 Reviews)
House
Home w/Beach Access Boat Slip Basketball Court
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Pier Relaxation! @ the Chesapeake Bay! From US $323
         

10.0 (2 Reviews)
House
Pier Relaxation! @ the Chesapeake Bay!
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Selloffcruises makes it easy to compare the best listings on Selloffcruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Selloffcruises 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

Top Attractions Around Shadyside Park, MD

Selloffcruises offers a large selection of top attractions around Shadyside Park. Research things to do on your vacation before you visit Shadyside Park.


U.S. Naval Academy Westfield Annapolis Mall Annapolis City Dock Chesapeake Beach Water Park Anne Arundel Medical Center Maryland State House Navy-Marine Corps Memorial Stadium Rod n Reel Charter Fishing Annapolis Harbour Center Kunta Kinte–Alex Haley Memorial Annapolis Maritime Museum Maryland Quiet Waters Park St John's College Maryland World War II Memorial William Paca House Renditions Golf Club The Kunta Kinte Alex Haley Memorial Maryland Hall for Creative Arts Thurgood Marshall Memorial Annapolis Bowl

Shadyside Park Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Shadyside Park?

Currently, the total number of properties listed in 2026 is over 52 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.