50+ Private Villas and Holiday Rentals in Shady Side |
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Shady Side Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Shady Side

Discover more than 50 vacation rentals available in Shady Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Shady Side.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Shady Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Shady Side. On average, places to stay near Shady Side offer 1172.2 ft², with nightly prices averaging US $552.

With Casai, finding and comparing holiday rentals in Shady Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Shady Side

Type Count
Vacation Homes 39
Cottages 5
Holiday Apartments 4

Use these Quick Filters to Find a Holiday Rental in Shady Side

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Shady Side.

Weather in Shady Side, MD

View the weather forecast for Shady Side before booking your Shady Side 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 Shady Side, MD

Casai offers a large selection of top attractions around Shady Side . Research things to do on your vacation before you visit Shady Side.


Shadyside Park
Captain Avery Museum
FedEx Field
U.S. Naval Academy
Six Flags America
Westfield Annapolis Mall
Annapolis City Dock
Chesapeake Bay Bridge
Sandy Point State Park
Show Place Arena
Bowie State University
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
St. Michaels Winery
Prince George's Community College

Other Places to Stay in Shady Side, MD


Captain Avery Museum 38 Properties
Shadyside Park 36 Properties

Frequently Asked Questions About Shady Side?

What are the top holiday rentals in Shady Side?

With numerous options available in Shady Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Shady Side:

Which holiday homes in Shady Side are best for families?

If you're searching for a family-friendly holiday home in Shady Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Shady Side:

How many Casai.com holiday rentals are available in Shady Side?

As of 2025, Casai boasts over 50 properties listed in the Shady Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Shady Side.


People Also Ask

There are 50 Shady Side, MD Holiday Rentals

Recently Booked Holiday Rentals in Shady Side