Photo by Hayley Gallagher

Shadyside holiday homes

We found 135 holiday rentals — enter your dates for availability

Discover a selection of 16 homes, 32 apartments and other holiday rentals in Shadyside that are perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll have the amenities that you expect and more, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Shadyside

Showing deals for:19 Dec - 26 Dec
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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Shadyside

  • Shadyside Art Festival: Experience the vibrant local art scene at this popular annual event showcasing talented artists and craftspeople.
  • Quaint Shops: Stroll through charming boutiques and unique shops, perfect for picking up local treasures.
  • Diverse Eateries: Enjoy a wide range of dining options, from casual cafes to fine dining, reflecting the area's cultural diversity.
  • Scenic Surroundings: Discover beautiful parks and picturesque streets, ideal for leisurely walks and family outings.
  • Local Culture: Immerse yourself in the friendly community vibe and explore nearby attractions that highlight Shadyside's heritage.

Top attractions near Shadyside

Shadyside, Pittsburgh, is perfect for city-themed and family vacations, offering a blend of culture and local charm. You can explore modern colleges, entertainment arenas, and beautiful churches. Don't miss the Shadyside Art Festival, quaint shops, and the vibrant village of Shadyside. This area caters to a variety of travellers, making it an ideal destination for a memorable experience.

  • University of Pittsburgh: A vibrant institution with stunning architecture and a lively atmosphere. Explore the beautiful campus, home to the renowned Cathedral of Learning, and enjoy a taste of local student life.
  • PPG Paints Arena: A dynamic venue, perfect for family entertainment. Catch a thrilling sports event or concert in this state-of-the-art arena, known for its electric atmosphere and diverse programming.
  • David L Lawrence Convention Center: A hub for business events, this impressive venue features modern facilities and hosts various conferences. Experience the professional vibe and the bustling energy of networking.

Things to do recommended for couples

For a romantic getaway in Shadyside, take a ride on the Monongahela Incline for stunning views, enjoy a luxurious day at Oakmont Country Club, or catch a live show at Roxian Theatre. Each experience offers a unique charm, perfect for couples looking to connect and create lasting memories.

Things to do recommended for families

Your family will have a fantastic time exploring the exciting Acrisure Stadium and the thrilling Sandcastle Water Park, both only 6.4km from Shadyside. For a relaxing day, head to Schenley Park, just 1.6km away, where you can unwind amidst nature's beauty.

Things to do recommended for groups

Groups visiting Shadyside can enjoy a vibrant shopping experience at The Waterfront, embark on scenic hikes along the Three Rivers Heritage Trail, or immerse themselves in culture and entertainment at the cozy Kelly Strayhorn Theater, all offering unique local vibes.

*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 around Shadyside

When you're planning a trip—whether with a group, family, pets, or for an extended stay—it's important to set your priorities straight while filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Shadyside with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for these features and more on Vrbo.
  • Traveling to Shadyside with young kids: Heading off on holiday with little ones can be a bit tricky. It’s important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, keeping in mind your closeness to family-friendly attractions is a smart move.
  • Taking your pets with you to Shadyside: For many families, a trip wouldn’t feel complete without their furry companion by their side. If that resonates with you, take a look at 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 Shadyside: If you're seeking holiday rentals with special offers 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Shadyside

Shadyside, a charming neighbourhood in Pittsburgh's East End, offers a delightful blend of urban vibes and family-friendly atmospheres. With its friendly locals and scenic surroundings, it's an ideal spot for any traveller. Explore the local shops, dine at delightful eateries, and soak in the vibrant culture. Nearby attractions and the Shadyside Chamber provide a rich experience, making it a perfect base for your adventures in this welcoming part of Pennsylvania.

  • Pittsburgh: Pittsburgh, a vibrant metropolis, offers a unique blend of urban charm and outdoor adventures. Located in the heart of Pennsylvania, Shadyside is one of its picturesque neighbourhoods. Visitors flock to Pittsburgh for family-friendly activities, city exploration, and outdoor experiences. Highlights include the renowned PPG Paints Arena for sports events, a variety of shopping centres, and educational attractions such as modern universities. Don’t miss the iconic stadiums that reflect the city’s rich sporting culture, making it a must-visit for any sports enthusiast.
  • Downtown Pittsburgh: Just 4.8km from Shadyside, Downtown Pittsburgh is the bustling heart of the city, renowned for its family-friendly atmosphere and vibrant sports scene. This area features a mix of arena entertainment venues, educational institutions, and shopping malls, catering to all types of visitors. Local landmarks include expansive urban parks where you can unwind amidst nature, as well as impressive stadiums showcasing the city’s sports pride. Whether you're catching a game or exploring local shops, Downtown offers an exciting urban experience.
  • Squirrel Hill: Located a mere 1.1km from Shadyside, Squirrel Hill is a charming neighbourhood celebrated for its cultural richness and family-oriented vibe. Visitors can enjoy a variety of educational and shopping experiences, making it a delightful spot to explore. The area boasts proximity to modern colleges and sports facilities, providing a lively atmosphere brimming with youthful energy. With its diverse dining options and community events, Squirrel Hill invites you to immerse yourself in local culture while enjoying a leisurely day out.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.6°F (-1.9°C)Light RainMostly CloudySlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyAverage
March40.5°F (4.7°C)Light RainMostly CloudyAverage
April51.1°F (10.6°C)Light RainMostly CloudySlightly High
May61.7°F (16.5°C)Light RainMostly SunnyAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly High
August72.1°F (22.3°C)Light RainMostly SunnyAverage
September66.2°F (19.0°C)Light RainMostly SunnySlightly High
October54.7°F (12.6°C)Light RainMostly SunnyAverage
November42.6°F (5.9°C)Light RainMostly SunnySlightly Low
December35.2°F (1.8°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Are you keen to save some cash on your next adventure? Being flexible with your travel dates can really help, as prices often vary. Additionally, if you opt for a longer stay, you’re likely to enjoy significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for you to plan new adventures, resume your previous arrangements, or review and organise your travel plans. You can easily find your saved or booked properties sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in Shadyside?
Houses are the most popular style of holiday home in Shadyside, according to our data. Even if you've got a different idea about what you'd like, Bookabach has properties in loads of sizes and shapes. Compare our options to find your ideal fit.
How much does it cost to rent a holiday home in Shadyside?
Different things affect what you'll pay for your holiday home in Shadyside, like the time of year, property type and length of stay. But, all of our holiday 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 holiday home. Enter your Shadyside travel dates to see your options on Bookabach. 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 holiday home.
Are there pet-friendly holiday homes 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 holiday homes on Bookabach. Simply enter your dates and destination, then check the "Pets allowed" filter box.
What are popular home amenities in Shadyside?
A barbecue grill, nearby museums and a garden are the most popular home amenities in Shadyside. Whether you plan to go by yourself, with your other half or a group of best friends, Bookabach will help you find a holiday home that suits your style with all the conveniences you're looking for.
Are there large group holiday homes in Shadyside?
Yes, you can choose one of three holiday homes 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 holiday homes in Shadyside that welcome kids?
Shadyside has eight family-friendly holiday 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 Centre
  • Carnegie Museum of Natural History

Can I find two-bedroom holiday homes in Shadyside?
Shadyside has four two-bedroom holiday properties for you to pick from. Book a holiday home with all the space and comfort you're looking for at an attractive price on Bookabach.
Are there holiday homes with WiFi in Shadyside?
Shadyside has three holiday homes with WiFi, so you can stay connected while on holiday. 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 Bookabach homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Shadyside?
Choose from seven holiday homes 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 holiday home in Shadyside?
We recommend you check with the Shadyside holiday property you're considering on Bookabach as age restrictions vary. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Shadyside for?
How long you can rent a holiday home 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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