50+ Rental Villas and Private Getaways in Shady Side |
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Shady Side Vacation Rentals & One Degree Stays Homes

About Shady Side Vacation Rentals

There are more than 50 vacation rentals that are available in Shady Side. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Shady Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Shady Side, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Shady Side. Places to stay near Shady Side are 1365.95 ft² on average, with prices averaging US $520 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Shady Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Shady Side

Type Count
Vacation Homes 39
Cottages 5
Holiday Apartments 4

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

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

OneDegreeStays 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 vacation rentals in Shady Side?

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:

Which vacation homes in Shady Side are best for families?

If you are looking for a family-friendly vacation home in Shady Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Shady Side:

How many onedegreestays vacation rentals are available in Shady Side?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 50 in the Shady Side area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Shady Side. 


People Also Ask

There are 50 Shady Side, MD Vacation Rentals

Recently Booked Vacation Rentals in Shady Side