Photo by Hayley Gallagher

Shadyside vacation rentals

We found 199 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 14 - Nov 21
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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 in Shadyside?
In Shadyside, apartments are the most popular type of vacation rental, with around 16 available in the area. These apartments are typically situated in charming neighbourhoods close to local shops, cafes, and parks, providing guests with a vibrant atmosphere. Most rooms come with essential amenities such as fully equipped kitchens, comfortable living areas, and often include features like air conditioning and laundry facilities.
How much does it cost to rent a vacation home in Shadyside?
Prices for vacation rentals in Shadyside 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 travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Shadyside to more spacious homes.
Are there any discounts for Shadyside vacation house rentals?
You can find great discounts on house rentals in Shadyside 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.
Are there any Shadyside vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Shadyside with parking available—perfect for families or travellers 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.
Can I find long-stay vacation rentals in Shadyside?
A long-stay vacation rental in Shadyside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Shadyside for a vacation rental?
April is the most popular month to visit Shadyside, as the vibrant spring season brings a burst of colour and life to the area. From March to May, this peak season attracts visitors eager to explore the charming streets, lush parks, and local boutiques, all while enjoying the mild weather that typically hovers around the low 15s Celsius. This is an ideal time for outdoor activities, including leisurely strolls through Shadyside's beautiful neighbourhoods and visits to nearby attractions.

As the flowers bloom and trees regain their foliage, the atmosphere becomes particularly inviting. April offers a comfortable climate for sightseeing and outdoor dining, with many cafes and restaurants featuring lovely patios to soak in the spring sunshine.

For those seeking a more budget-friendly option, December is a wonderful time to visit Shadyside as well, when the vacation decorations create a magical ambience. This quieter month allows for a more relaxed exploration of the area, with local shops offering unique gifts and festive experiences.
Are there any remote work vacation rentals in Shadyside?
In Shadyside, Pennsylvania, there are around 29 vacation rentals that cater specifically to remote work needs. This vibrant neighbourhood, known for its charming tree-lined streets and proximity to shops and cafes, provides an ideal setting for those looking to combine work and leisure. Many of these properties offer dedicated workspaces, including desks and office chairs, as well as high-speed Wi-Fi to ensure productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Shadyside vacation rental?
Book your Shadyside 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 Shadyside?
In Shadyside, visitors can enjoy a range of attractions that highlight the neighbourhood's charm and vibrant community. The area is known for its beautiful tree-lined streets and historic architecture, making it ideal for leisurely strolls. Shadyside is home to the renowned Shadyside Shopping District, featuring a variety of boutiques, cafes, and restaurants, great for exploring local culture and cuisine.

Nearby, visitors can enjoy the lush greenery of Mellon Park, which offers walking paths, gardens, and sports facilities, providing a serene escape within the urban landscape. The neighbourhood is also conveniently located near the University of Pittsburgh and Carnegie Mellon University, adding a youthful energy and numerous cultural events to the area.
Can I change or cancel my Shadyside home rental booking on Vrbo?
To find Shadyside 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 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 travellers 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 cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Shadyside 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.

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