Shady Side holiday homes

We found 632 holiday rentals — enter your dates for availability

Discover a selection of 11 homes and other holiday rentals in Shady Side that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you expect for your stay, which might include a garden and pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday 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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Shady Side

Do you want to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Shady Side has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Renditions Golf Club (9.7 mi / 15.6 km)
  • Chesapeake Beach Water Park (10.4 mi / 16.8 km)
  • U.S. Naval Academy Golf Club (11 mi / 17.6 km)
  • Maryland Renaissance Festival (11.5 mi / 18.6 km)
  • Lake Presidential Golf Club (11.7 mi / 18.9 km)
  • Six Flags America (14.9 mi / 24 km)

Exploring the natural landscape of Shady Side

Whether you're an active traveller or just want to spend some time taking in the scenery, Shady Side is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Shadyside Park (0.4 mi / 0.6 km)
  • Triton Beach (3 mi / 4.9 km)
  • Maryland Quiet Waters Park (7.1 mi / 11.4 km)
  • Bay Ridge Beach (7.9 mi / 12.7 km)
  • Sandy Point Beach (13.3 mi / 21.4 km)
  • Allen Pond Park (13.6 mi / 21.8 km)

Transport 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 centre. If you're unable to find a flight that fits your schedule, 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 holiday home accommodation in Shady Side?
Houses are the most popular style of holiday home in Shady Side, according to our data. Even if you have a different vision in mind, Bookabach 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 holiday home in Shady Side?
The average price for a holiday home 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 cosy 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 travelling. All you have to do is enter your travel dates into Bookabach 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 holiday homes in Shady Side?
You’re in luck! There are. You can pick from seven holiday homes that allow pets in Shady Side. Several of our pet-friendly holiday homes 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 Bookabach.
What are popular home amenities in Shady Side?
A fireplace, a firepit and a garden are the most popular home amenities in Shady Side. Whether you’re heading away by yourself, with your spouse or a group of family members, Bookabach can help you find a holiday home that suits your style with a load of extras you’ll love.
Are there large group holiday homes in Shady Side?
Take your pick of six Bookabach holiday homes 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 holidaying with — and no one else.
Are there holiday homes in Shady Side that welcome kids?
With seven family-friendly holiday 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 holidaying 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 holiday is a snap with these leading family-friendly attractions:

  • Annapolis Maritime Museum
  • Triton Beach
  • Annapolis Sailing School

Are there holiday homes with WiFi in Shady Side?
Whether you want to keep up with the headlines, look over emails or surf social media, there are six holiday homes with WiFi in Shady Side. Check the “WiFi” box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in Shady Side?
You’ll find seven holiday homes 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 holiday home in Shady Side?
The minimum age is normally 16, 18 or 21. It can change from property to property on Bookabach, so look at the rules of your preferred Shady Side holiday home before making a booking.
How long can I rent a holiday home in Shady Side for?
The amount of time you can rent a Shady Side holiday 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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