Photo by Hayley Gallagher

Shadyside vacation rentals

We found 203 vacation rentals — enter your dates for availability

Discover a selection of 14 homes, 23 apartments, and other vacation rentals in Shadyside that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Shadyside

Showing deals for:Nov 7 - Nov 14
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Find out more about Shadyside

Find out more about Shadyside

Why visit Shadyside

  1. Urban Charm: Experience Shadyside's vibrant atmosphere, blending modern culture with local charm.
  2. Shopping and Dining: Explore a bustling business district filled with unique boutiques and delightful cafes.
  3. Family-Friendly Activities: Enjoy various attractions suitable for all ages, making it perfect for family vacations.
  4. Nearby Neighbourhoods: Visit nearby areas like Squirrel Hill and East Liberty for additional cultural experiences.
  5. Diverse Accommodations: Find a range of lodging options, from cozy apartments to spacious vacation homes.

Popular types of accommodation around Shadyside

Planning a getaway to Shadyside? You're in for a treat! This charming neighbourhood offers a variety of accommodation options, including houses, apartments, and cottages. Whether you're seeking a cozy apartment in Shadyside or a spacious rental for the whole family, you'll find the perfect spot to unwind. Explore Shadyside apartment rentals and discover the ideal home away from home for your Canadian adventure!

  • Houses: The top choice for visitors in Shadyside, ideal for families or groups seeking a spacious and private stay.
  • Apartments: A popular option for those looking for convenience and comfort, perfect for solo travellers or couples.
  • Cottages: A charming alternative, offering a cozy retreat with a unique character for a peaceful getaway.
  • Condos: Modern and well-equipped, condos provide a stylish living space in the heart of Shadyside.
  • Cabins: A delightful choice for nature lovers, cabins offer a rustic experience close to outdoor adventures.**

Top attractions around Shadyside

Shadyside, Pittsburgh, is a fantastic destination for city-themed, family, and business vacations. With attractions like modern colleges, entertainment arenas, and beautiful churches, there's plenty to explore. Whether you're seeking cultural experiences or family-friendly activities, Shadyside offers a vibrant atmosphere that caters to diverse interests. Be sure to take in the unique blend of urban charm and local culture during your visit.

  1. Carnegie Mellon University: Experience the vibrant atmosphere of this prestigious university, known for its cutting-edge research and innovative programs. Explore the beautiful campus, filled with modern architecture and green spaces, reflecting a lively city vibe.
  2. PPG Paints Arena: Enjoy thrilling events at this family-friendly arena, home to exciting sports and concerts. The energetic atmosphere makes it a perfect spot for entertainment enthusiasts, where unforgettable memories are created.
  3. David L Lawrence Convention Center: Discover this bustling venue tailored for business events and conferences. Its striking architecture and versatile spaces cater to various professional gatherings, embodying a dynamic business vibe.

Things to do recommended for couples

For a romantic getaway in Shadyside, take a scenic ride on the Monongahela Incline, indulge in luxury at the Oakmont Country Club, or enjoy live music at the Rex Theater. Each offers a unique atmosphere perfect for couples looking to create special memories together.

Things to do recommended for families

Families visiting Shadyside will love the excitement of Acrisure Stadium, the tranquility of Schenley Park, and the fun-filled adventures at Sandcastle Water Park. Enjoy a mix of sports, relaxation, and family entertainment all within a short distance from your accommodation.

Things to do recommended for groups

Explore the vibrant Waterfront shopping centre, only 4.8km from Shadyside, for a day of shopping and entertainment. Experience culture at the nearby Kelly Strayhorn Theater, 1.4km away, or embark on an adventurous hike along the scenic Three Rivers Heritage Trail, also 4.8km away.

What do I need to keep in mind when booking a vacation around Shadyside

If you’re travelling with a group, family, or pets, or if you’re considering longer stays, it's important to prioritise your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Shadyside with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Shadyside with young kids: Traveling with young children can present its unique challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Shadyside: For many, a family vacation isn't truly fulfilling without their beloved furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Shadyside: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. 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 as well.

Where to stay around Shadyside

Shadyside, a vibrant neighbourhood in Pittsburgh, offers a delightful blend of urban charm and family-friendly vibes. Explore its bustling business district, where local boutiques and cafes await. Nearby, you'll find popular areas like Squirrel Hill and East Liberty, each brimming with art, culture, and friendly faces. Whether you're on a family getaway or a business trip, Shadyside promises an enriching experience filled with warmth and creativity.

  • Downtown Pittsburgh: Located a mere 4.8km from Shadyside, Downtown Pittsburgh serves as the vibrant core of the city. Here, visitors can immerse themselves in a bustling atmosphere filled with family-friendly activities, sports events, and a dynamic urban experience. Explore the arena entertainment facility where you can catch a thrilling game or concert, and indulge in shopping at the expansive mall centre. Notable landmarks include the impressive stadiums and urban parks, perfect for a leisurely stroll or a family picnic.
  • Squirrel Hill: Just 1.1km away from Shadyside, Squirrel Hill is a charming neighbourhood renowned for its rich culture, family-friendly environment, and vibrant city life. This area offers a delightful array of educational institutions and shopping areas, making it a perfect spot for both learning and leisure. Visitors can explore the local modern college university, enjoy a game at the nearby stadium, or simply wander through the inviting streets filled with quaint shops and eateries.
  • Friendship: Also located 1.1km from Shadyside, Friendship combines family activities with a robust city vibe and a touch of business efficiency. This lively neighbourhood features numerous educational opportunities and a variety of shopping options. Key attractions include a modern college university, bustling shopping areas, and a serene urban park, providing a perfect blend of relaxation and exploration for visitors of all ages.

Best time to go to Shadyside

If you're planning a trip to Shadyside, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.6°F (-1.9°C)Light RainMostly CloudySlightly LowSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly CloudyAverageSlightly Low
April51.1°F (10.6°C)Light RainMostly CloudySlightly HighAverage
May61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverageSlightly High
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighAverage
August72.1°F (22.3°C)Light RainMostly SunnyAverageAverage
September66.2°F (19.0°C)Light RainMostly SunnySlightly HighAverage
October54.7°F (12.6°C)Light RainMostly SunnyAverageSlightly High
November42.6°F (5.9°C)Light RainMostly SunnySlightly LowSlightly High
December35.2°F (1.8°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new getaways, pick up right where you left off, or review and arrange your travel plans. You can easily find the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Shadyside?
Houses are the most popular style of vacation rental in Shadyside, according to our data. Even if you've got a different idea about what you'd like, Vrbo has properties in loads of sizes and shapes. Compare our options to find your ideal fit.
How much does it cost to rent a vacation rental in Shadyside?
Different things affect what you'll pay for your vacation rental in Shadyside, like the time of year, property type and length of stay. But, all of our vacation homes have something in common — exceptional value. Simply add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Shadyside?
When you travel and the size and style of the property will help determine the cost of your beachside vacation rental. Enter your Shadyside travel dates to see your options on Vrbo. Looking for a backyard so the kids can run around, or a pool to keep them busy? Use the filters to select the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Shadyside?
Pack a travel bag for your pooch because Shadyside has eight stays that throw out the welcome mat to doggie guests. Let your four-legged buddy have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates and destination, then check the "Pets allowed" filter box.
What are popular rental amenities in Shadyside?
A barbecue grill, nearby museums and a garden are the most popular rental amenities in Shadyside. Whether you plan to go by yourself, with your other half or a group of best friends, Vrbo will help you find a vacation home that suits your style with all the conveniences you're looking for.
Are there large group vacation rentals in Shadyside?
Yes, you can choose one of three vacation rentals in Shadyside that can accommodate a group of five or more guests. From family get-togethers to special occasions, these stays have ample space to chill out with the people you love.
Are there vacation rentals in Shadyside that welcome kids?
Shadyside has eight family-friendly vacation homes. And discovering a stay that welcomes children is a breeze with our "Properties good for families" filter. Besides having the entire place to yourselves, you'll enjoy access to perks and amenities such as extra bedrooms, yards and private pools.
What are the top attractions for families in Shadyside?
You'll find loads of fun things to do and see with the family in Shadyside, such as:

  • Pittsburgh Zoo and PPG Aquarium
  • Carnegie Science Center
  • Carnegie Museum of Natural History

Can I find two-bedroom vacation rentals in Shadyside?
Shadyside has four two-bedroom vacation properties for you to pick from. Book a vacation home with all the space and comfort you're looking for at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Shadyside?
Shadyside has three vacation rentals with WiFi, so you can stay connected while on vacation. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to scrolling social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Shadyside?
Choose from seven vacation rentals with air conditioning in Shadyside providing that cool, cool breeze and extra level of comfort. Simply enter your preferred travel dates and then make use of our filters to help you book properties with air conditioning.
How old do you have to be to rent a vacation rental in Shadyside?
We recommend you check with the Shadyside vacation property you're considering on Vrbo as age restrictions vary. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Shadyside for?
How long you can rent a vacation rental in Shadyside varies according to the property. Just enter your chosen dates to view a list of options offering extended stays. With tons of amenities such as air conditioning and laundries, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Shadyside.

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