Shady Side vacation rentals

We found 601 vacation rentals — enter your dates for availability

Discover a selection of 11 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.

Vacation rentals with weekly discounts - Shady Side

Showing deals for:Jul 10 - Jul 17

Image gallery for Captain's Retreat! Newly Renovated - few steps from the beach!

Exterior
9.8 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)

Captain's Retreat! Newly Renovated - few steps from the beach!

Annapolis

17% off
Price is $800
$5,603 for 7 nights
All fees included
Captain's Retreat! Newly Renovated - few steps from the beach!

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Shady Side

Why visit Shady Side

  • Scenic Outdoor Activities: Enjoy the beauty of Shady Side Park and nearby sandy beaches, perfect for family-friendly fun.
  • Waterfront Community Charm: Experience the welcoming atmosphere of this picturesque waterfront community with cozy vacation rentals.
  • Historic Attractions: Visit local historic houses and take guided tours to learn about the area's rich history.
  • Urban Cultural Experiences: Take a short trip to Camden Yards for a taste of urban culture and entertainment.
  • Friendly Locals: Engage with the welcoming residents who enhance the overall vacation experience.

Popular types of accommodation in Shady Side

Planning a getaway to Shady Side? Discover the charm of this waterfront community with a variety of vacation rentals to suit your needs. From cozy cottages and spacious houses to comfortable apartments, Shady Side has something for everyone. Explore our selection of Shady Side homes and find the perfect house for your stay in this beautiful Maryland destination.

  • Houses: A favorite among visitors to Shady Side, these homes offer spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Cottages: These quaint, cozy retreats are perfect for those wanting a charming and intimate getaway in a picturesque setting.
  • Apartments: An excellent choice for solo travelers or couples, providing convenient access to local attractions and amenities.
  • Condos: These modern options combine luxury and comfort, making them a popular choice for vacationers.
  • Cabins: Perfect for nature enthusiasts, cabins offer a rustic experience amidst scenic surroundings.**

Top attractions in and around Shady Side

Shady Side, Maryland, is an ideal destination for outdoor enthusiasts and families seeking scenic experiences. Visitors can explore local attractions such as historic houses, urban parks, and marinas. Don’t miss Shady Side Park and the beautiful Eastern Shore. For a taste of urban culture, consider a trip to Camden Yards, and explore rental options by neighborhood. Guided tours are also available for those looking to enhance their visit.

  • Shadyside Park: This urban park is a delightful spot within Shady Side, perfect for families and outdoor enthusiasts. Enjoy its green spaces, play areas, and scenic walking paths that create a relaxed atmosphere.
  • Annapolis City Dock: Located 10 miles away, this historic dock offers beautiful waterfront views and a vibrant atmosphere, ideal for leisurely strolls, dining, and exploring local shops.
  • Anne Arundel Medical Center: Situated 10 miles from Shady Side, this medical center combines a professional environment with family-friendly services, making it a unique community hub.

Things to do recommended for couples

For a romantic getaway in Shady Side, consider a visit to the Old South Country Club, located 8 miles away. Enjoy the luxurious ambiance while indulging in fine dining and picturesque views, perfect for a couple's escape.

Things to do recommended for families

Families can explore the scenic views at the Chesapeake Bay, enjoy a day of fishing or crabbing, and visit the nearby parks for picnics and nature walks. The local community often hosts family-friendly events, providing a perfect blend of relaxation and adventure.

Things to do recommended for groups

Explore the scenic beauty of Chesapeake Bay with a group kayak tour, or enjoy a delightful picnic at the nearby Sandy Point State Park. You can also visit local seafood markets to taste the freshest catches from the bay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Shady Side

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Shady Side with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Shady Side with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is beneficial.
  • Taking your pets with you to Shady Side: For many, a family vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Shady Side: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the right destination. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Shady Side

Shady Side, Maryland, offers a delightful vacation experience filled with outdoor adventures and scenic views. Enjoy family-friendly activities along its residential streets, explore the nearby sandy beaches, and soak in the relaxing atmosphere. Just a short drive away, visit Fort Meade for a touch of history. With friendly locals and a welcoming vibe, Shady Side is perfect for a memorable getaway that blends leisure and exploration.

  • Annapolis: Located 10 miles from Shady Side, Annapolis is the charming capital of Maryland, renowned for its rich history and vibrant waterfront. Visitors are drawn to its blend of family-friendly activities and outdoor experiences. The city features historic landmarks like the U.S. Naval Academy, picturesque views of the Chesapeake Bay, and lovely beaches. Annapolis boasts a variety of shopping options, from quaint boutiques to bustling shopping centers. Whether you're exploring the historic district or enjoying a meal at a waterfront restaurant, Annapolis offers a delightful urban escape with a maritime flair.
  • Upper Marlboro: Situated 13 miles from Shady Side, Upper Marlboro offers a unique mix of family-oriented and outdoor activities. This city is home to several shopping centers and educational institutions, making it a convenient destination for travelers. Highlights include the local sports facilities and stadiums that host various events throughout the year. Upper Marlboro's urban parks provide ample green spaces for picnics and recreation, making it an ideal spot for families looking to unwind and enjoy the outdoors. With its community spirit and engaging attractions, Upper Marlboro is worth exploring.
  • Galesville: Just 2 miles from Shady Side, Galesville is a quaint town that captures the essence of scenic beauty and outdoor adventure. Visitors can enjoy recreational areas and urban parks, perfect for family outings and leisurely strolls. The picturesque views of the bay and nearby beaches enhance its appeal, offering a serene atmosphere for relaxation. Galesville is also known for its educational facilities and charming shopping centers. Whether you're kayaking in the bay or enjoying a picnic in the park, Galesville provides a peaceful retreat close to nature.

Best time to go to Shady Side

If you're planning a trip to Shady Side, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.8°F (2.1°C)Light RainMostly SunnyAverageSlightly Low
February38.1°F (3.4°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.2°F (17.9°C)Light RainMostly SunnySlightly HighAverage
June73.0°F (22.8°C)Light RainMostly SunnySlightly HighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnySlightly HighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyAverageSlightly High
September70.7°F (21.5°C)Light RainMostly SunnyAverageAverage
October60.4°F (15.8°C)Light RainMostly SunnySlightly LowAverage
November48.7°F (9.3°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can lead to better pricing, as rates often fluctuate. Additionally, booking a longer stay can result in considerable savings. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides an organized space for you to initiate new travel plans, revisit your existing arrangements, or manage your bookings efficiently. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Renditions Golf Club (9.7 mi / 15.6 km)
  • Chesapeake Beach Water Park (10.4 mi / 16.8 km)
  • Maryland Renaissance Festival (11.5 mi / 18.6 km)
  • St. Michaels Winery (16.2 mi / 26 km)
  • South River Golf Links (6.3 mi / 10.1 km)
  • U.S. Naval Academy Golf Club (11 mi / 17.6 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:

  • 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)
  • Carrs Beach (8.1 mi / 13.1 km)
  • Northern Chesapeake Bay (12.4 mi / 19.9 km)
  • Sandy Point Beach (13.3 mi / 21.4 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 best area to stay in Shady Side, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Shady Side, Maryland, the best area to stay is near the waterfront neighborhoods, which offer stunning views and a charming atmosphere. This area is particularly appealing for those looking to enjoy outdoor activities and the natural beauty of the Chesapeake Bay. You'll find various properties along the shoreline, providing easy access to water-related fun.

One of the top attractions in this area is the Chesapeake Bay, where you can enjoy boating, fishing, and kayaking. The nearby parks also offer scenic trails for hiking and birdwatching. Additionally, the local community hosts events that celebrate the maritime culture, giving visitors a taste of the area's rich history and vibrant lifestyle.

In terms of accommodation options, there are several vacation rentals available that cater to different preferences and budgets, allowing you to choose a cozy spot that fits your needs.
How much does it cost to rent a vacation home in Shady Side?
Prices for vacation rentals in Shady Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Shady Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Shady Side vacation house rentals?
You can find great discounts on house rentals in Shady Side on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Shady Side?
In Shady Side, vacation houses and cottages are the most popular types of rentals, with several options available throughout the area. These properties typically feature cozy living spaces, fully equipped kitchens, and outdoor areas, allowing guests to enjoy the scenic views of the Chesapeake Bay. Many vacation houses and cottages are situated in tranquil neighborhoods, providing a peaceful retreat for families or groups looking to explore the nearby waterfront and local parks.
Are there any family house rentals in Shady Side?
In Shady Side, Maryland, there are several family-friendly house rentals available, providing a great base for exploring the area's charm. Visitors can find homes with spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces superb for kids to play and enjoy the fresh air. Many properties also include amenities like Wi-Fi and comfortable furnishings to ensure a pleasant stay.

This quaint waterfront community is close to attractions such as the scenic Chesapeake Bay and nearby parks, offering opportunities for outdoor activities like hiking and fishing. Families can also enjoy the local atmosphere with quaint shops and dining options in the vicinity.
Can I find long-stay vacation rentals in Shady Side?
A long-stay vacation rental in Shady Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Shady Side?
In Shady Side, there are several pet-friendly house rentals available, making it an inviting destination for travelers with furry companions. Many of these vacation homes offer amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, great for families or groups looking to unwind.

The area is close to several parks and waterfront spots, providing ample opportunities for outdoor activities with pets. The nearby Broadneck Park features walking trails and open spaces, while the scenic Chesapeake Bay offers picturesque views and places for leisurely strolls.
Are there any remote work vacation rentals in Shady Side?
In Shady Side, Maryland, there are several vacation rentals that cater to remote workers. The area offers a range of properties equipped with essential amenities like free Wi-Fi in both rooms and public areas, ensuring that you can stay connected while enjoying your stay. Many rentals provide comfortable workspaces, allowing for productivity in a peaceful setting.

The picturesque surroundings of Shady Side, including its proximity to the Chesapeake Bay, make it an appealing destination for those looking to balance work with relaxation. Travelers can also explore local attractions such as parks and waterfront activities during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shady Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Shady Side with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Shady Side?
In Shady Side, popular rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals during their stay. Many rentals also feature decks or patios, providing outdoor spaces to relax and enjoy the scenic views of the surrounding area. Onsite parking is typically available, making it convenient for guests with vehicles. Additionally, coffee and tea makers are common, ensuring that guests can enjoy their morning beverages at their leisure.
When is the best time to visit Shady Side for a vacation rental?
July is the most popular month to visit Shady Side, Maryland, when the summer season is in full swing. This peak travel period, which spans from May to July, attracts families and outdoor enthusiasts eager to enjoy the region's beautiful waterfront and vibrant community events. Visitors can partake in a variety of activities, from kayaking on the Chesapeake Bay to exploring local parks and enjoying the picturesque scenery.

During July, temperatures typically range from the mid-70s to mid-80s Fahrenheit, providing a warm and inviting climate superb for outdoor adventures and sightseeing. The charming waterfront community offers ample opportunities for fishing, boating, and simply relaxing by the water's edge. Shady Side's friendly atmosphere and close-knit community make it an ideal destination for travelers seeking both adventure and relaxation.

If you're looking for a more cost-effective time to visit, consider planning your trip in December. While this month falls into the low season, it offers a unique charm with fewer crowds and a chance to enjoy the peaceful winter landscape. It can be a wonderful time for quiet reflection and enjoying cozy indoor activities.
How early should I book a Shady Side vacation rental?
Book your Shady Side vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Shady Side, Maryland, United States of America?
In Shady Side, Maryland, visitors can enjoy a range of attractions that highlight the area's natural beauty and maritime heritage. The Shady Side area is known for its waterfront charm, with the Chesapeake Bay providing opportunities for boating, fishing, and stunning sunset views. Vacation rentals near the Bay can offer easy access to local marinas and public docks, making it convenient for those looking to explore the water.

The nearby Jug Bay Wetlands Sanctuary is a significant ecological site where visitors can hike and observe diverse wildlife, including migratory birds and various plant species. This sanctuary is great for nature lovers and those who appreciate peaceful outdoor activities.

Another point of interest is the historic Deale area, just a short drive away, which features quaint shops and local eateries, allowing travelers to experience the local flavor. Additionally, the proximity to the larger town of Annapolis provides access to a wider array of attractions, including the U.S. Naval Academy and the vibrant waterfront district filled with shops and restaurants.
Can I change or cancel my Shady Side home rental booking on Vrbo?
To find Shady Side vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Shady Side vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas