51+ Vacation Home Rentals in Shady Side |
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  2. Maryland
  3. Shady Side

Shady Side Vacation Rentals & Ski-in/Ski-out Homes

About Shady Side Vacation Rentals

Explore over 51 vacation rentals in Shady Side with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Shady Side for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Shady Side. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Shady Side tailored to your preferences. On average, these rentals offer 1339.17 ft² of space, and are priced at an average of US $504 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Shady Side at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Shady Side

Type Count
Vacation Homes 40
Cottages 5
Holiday Apartments 4
Cabin Rentals 2

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

★ Pro Tip: Discover Your Ideal Vacation Rental in Shady Side with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

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

Sunski 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?

When organizing your trip to Shady Side, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Shady Side. Peruse our collection of highly-rated properties and secure your reservation today.

Which vacation homes or resorts in Shady Side are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Shady Side. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Shady Side?

Discover the ideal vacation rental in Shady Side with SunSki Resorts™. We provide an extensive selection of over 51 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Shady Side.


People Also Ask

There are 51 Shady Side, MD Vacation Rentals

Recently Booked Vacation Rentals in Shady Side