Shady Side vacation rentals

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your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 10 homes and other vacation rentals in Shady Side that are perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

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Choose a vacation rental for your Shady Side getaway

Enjoy the museums and other features of Shady Side. Renowned for its shopping, restaurants and parks, this city welcomes all visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Shady Side

Are you hoping to find top things to see and do while you're in town? Venture out of your vacation home and check out everything that makes Shady Side a fun place to get away. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chesapeake Beach Water Park (10.4 mi / 16.8 km)
  • Six Flags America (14.9 mi / 24 km)
  • St. Michaels Winery (16.2 mi / 26 km)
  • South River Golf Links (6.3 mi / 10.1 km)
  • Thurgood Marshall Memorial (9.5 mi / 15.4 km)
  • Renditions Golf Club (9.7 mi / 15.6 km)

Exploring the natural landscape of Shady Side

Whether you're an outdoor enthusiast or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Shady Side. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Maryland Quiet Waters Park (7.1 mi / 11.4 km)
  • Sandy Point Beach (13.3 mi / 21.4 km)
  • Sandy Point State Park (13.6 mi / 21.9 km)
  • Breezy Point Beach (15.3 mi / 24.6 km)
  • Patuxent River (25.4 mi / 40.8 km)
  • Shadyside Park (0.4 mi / 0.6 km)

Transportation options to and around Shady Side

Fly into Fort Meade, MD (FME-Tipton), the closest airport, located 21.6 mi (34.8 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into College Park, MD (CGS), which is 24.1 mi (38.7 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Shady Side?

Houses are the most popular style of vacation rental in Shady Side, according to our data. Even if you have a different vision in mind, Vrbo has properties in many sizes and shapes. Browse our many options to find your perfect Shady Side pad.

How much does it cost to rent a vacation rental in Shady Side?

The average price for a vacation rental in Shady Side can vary based on factors such as property type, season and length of stay. Whether you're searching for a sprawling villa with a pool or a cozy cottage for just you and your sweetheart, just add your dates of travel to see stays with unbeatable value.

How much does it cost to rent a beach house in Shady Side?

Prices for beach houses in Shady Side may vary depending on the size and type of the property and time of year you're traveling. All you have to do is enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use the filters to tailor your search by nearby activities, amenities, ratings and more.

Are there pet-friendly vacation rentals in Shady Side?

You're in luck! There are. You can pick from seven vacation rentals that allow pets in Shady Side. Several of our pet-friendly vacation rentals even come with a backyard for your furry pal to play around in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find a pad that'll get tails wagging on Vrbo.

What are popular rental amenities in Shady Side?

A fireplace, a firepit and a garden are the most popular rental amenities in Shady Side. Whether you're heading away by yourself, with your spouse or a group of family members, Vrbo can help you find a vacation rental that suits your style with a load of extras you'll love.

Are there large group vacation rentals in Shady Side?

Take your pick of six Vrbo vacation rentals in Shady Side that can accommodate a group of five or more people. You'll enjoy all the privacy and space you need to spend time with the people you're vacationing with — and no one else.

Are there vacation rentals in Shady Side that welcome kids?

With seven family-friendly vacation homes available in Shady Side, there's never been a better time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter to view stays that feature amenities perfect for vacationing families, like dining rooms, private pools, hot tubs and entertainment areas.

What are the top attractions for families in Shady Side?

Keeping the kids occupied during your Shady Side vacation is a snap with these leading family-friendly attractions:

  • Annapolis Maritime Museum
  • Triton Beach
  • Annapolis Sailing School

Are there vacation rentals with WiFi in Shady Side?

Whether you want to keep up with the headlines, look over emails or surf social media, there are six vacation homes with WiFi in Shady Side. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How can I find vacation rentals with air conditioning in Shady Side?

You'll find seven vacation rentals with air conditioning in Shady Side giving you that cool, cool breeze and extra comfort level. Enter your preferred dates of travel and then use our filter tool to find properties with air conditioning.

How old do you have to be to rent a vacation rental in Shady Side?

The minimum age is normally 16, 18 or 21. It can change from property to property on Vrbo, so look at the rules of your preferred Shady Side vacation home before making a booking.

How long can I rent a vacation rental in Shady Side for?

The amount of time you can rent a Shady Side vacation home for depends on each property. Simply tap in your preferred travel dates to view options that offer extended stays. They come with all you require to make your extended break more comfortable and enjoyable, such as kitchens and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can stick around for longer for less.

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