56+ Rental Villas and Private Getaways in Shady Side |
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Shady Side Villa Rentals

About Shady Side Vacation Rentals

There are more than 56 incredible getaway rentals that are available in Shady Side. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Shady Side.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Shady Side, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Shady Side. Places to stay near Shady Side are 1289.29 ft² on average, with prices averaging $528 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Shady Side. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Shady Side

Type Count
Vacation Homes 45
Cottages 5
Holiday Apartments 4
Cabin Rentals 2

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

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Shady Side with BedroomVillas.

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

Stay Near Shady Side's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Shady Side's Research Top Attractions For Your Vacation


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

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Captain Avery Museum 38 Properties
Shadyside Park 36 Properties

Frequently Asked Questions About Shady Side?

What are the top hotels or resorts in Shady Side?

We provide an array of great vacation destinations in Shady Side. If you are looking to stay in or around the Shady Side area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Shady Side:

Which hotel or resort in Shady Side is best for families?

Searching for a family-friendly getaway in Shady Side? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Shady Side?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 56 in the Shady Side area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Shady Side. 


People Also Ask

Hotels in Shady Side and 51 rentals

Recently Booked Hotels, Resorts, or Rentals in Shady Side