Shadyside, Pittsburgh holiday homes: holiday houses & more

Discover a selection of 16 homes, 24 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:12 Sept - 19 Sept

Wonderful

(10 reviews)

Ind Loft Children's Hospital Shadyside Oakland 4

Pittsburgh, Pennsylvania

10% off

NZ$409 per night

includes taxes & fees

Exceptional

(46 reviews)

New Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft

Pittsburgh, Pennsylvania

10% off

NZ$1,488 per night

includes taxes & fees

Exceptional

(21 reviews)

Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

Pittsburgh, PA

8% off

NZ$1,268 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Shadyside

Showing deals for: 12 Sept - 15 Sept

Pittsburgh Vacation Rental | 2BR | 1BA | 650 Sq Ft | Access By Stairs

Walk to Walnut St: Pet-Friendly Pittsburgh Home!

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

NZ$613 per night

includes taxes & fees

Large open area from the kitchen to dining and living areas

👑King Bed⚡ Quiet West Penn🏥 Parking 🐶Pets

Sleeps 9 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$1,224 per night

includes taxes & fees

Pittsburgh Vacation Rental | 2BR | 2BA | 1,200 Sq Ft | Stairs Required

Walk to Walnut St: ‘Shadyside House’ w/ Deck

Sleeps 8 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$657 per night

includes taxes & fees

Top rated rentals - Shadyside

Wonderful time

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

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.