Photo by Hayley Gallagher
Shadyside holiday homes
We found 208 holiday rentals — enter your dates for availability
Discover a selection of 15 homes, 15 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:18 Jul - 25 Jul
Image gallery for *New* Loft 3 min to CMU, Pitt Sleeps 4

9.89.8 out of 10 rating
Exceptional
(6 reviews)
*New* Loft 3 min to CMU, Pitt Sleeps 4
Pittsburgh, Pennsylvania
8% off
Price is NZ$2,224
NZ$2,224
NZ$318 per night
includes taxes & fees
Image gallery for 5 King Bed Family Home - Frick Park - Bakery Square

1010 out of 10 rating
Exceptional
(9 reviews)
5 King Bed Family Home - Frick Park - Bakery Square
Pittsburgh, PA
12% off
Price is NZ$6,529
NZ$6,529
NZ$933 per night
includes taxes & fees
Image gallery for Ind Loft Children's Hospital Shadyside Oakland 4

9.09.0 out of 10 rating
Wonderful
(10 reviews)
Ind Loft Children's Hospital Shadyside Oakland 4
Pittsburgh, Pennsylvania
9% off
Price is NZ$2,563
NZ$2,563
NZ$366 per night
includes taxes & fees
Image gallery for Pittsburgh Delight - Cozy 2B/1B Apt w/ Private Parking, Second Floor Unit

1010 out of 10 rating
Exceptional
(9 reviews)
Pittsburgh Delight - Cozy 2B/1B Apt w/ Private Parking, Second Floor Unit
Pittsburgh, PA
7% off
Price is NZ$3,097
NZ$3,097
NZ$442 per night
includes taxes & fees
Image gallery for Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf

9.49.4 out of 10 rating
Exceptional
(20 reviews)
Best skyline view of CMU/PITT Historical Oakland 5BR storybook house 3000sf
Pittsburgh, PA
8% off
Price is NZ$7,098
NZ$7,098
NZ$1,014 per night
includes taxes & fees
Image gallery for *New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft

9.89.8 out of 10 rating
Exceptional
(41 reviews)
*New* Huge! Spacious 3 Bedroom in Oakland that sleeps 12! over 3000+ sq ft
Pittsburgh, Pennsylvania
10% off
Price is NZ$9,424
NZ$9,424
NZ$1,346 per night
includes taxes & fees
Image gallery for Downtown Escape: 3Br - Game/Movie Room - Foosball

8.88.8 out of 10 rating
Excellent
(6 reviews)
Downtown Escape: 3Br - Game/Movie Room - Foosball
Pittsburgh, PA
7% off
Price is NZ$4,787
NZ$4,787
NZ$684 per night
includes taxes & fees
Image gallery for Modern ✌🏾Bedroom House in the ❤️ of Shadyside

9.89.8 out of 10 rating
Exceptional
(33 reviews)
Modern ✌🏾Bedroom House in the ❤️ of Shadyside
Pittsburgh, PA
7% off
Price is NZ$2,479
NZ$2,479
NZ$354 per night
includes taxes & fees
Image gallery for Hillman Cancer Center/Children Hospitals Sleeps 6

9.29.2 out of 10 rating
Wonderful
(11 reviews)
Hillman Cancer Center/Children Hospitals Sleeps 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$2,689
NZ$2,689
NZ$384 per night
includes taxes & fees
Image gallery for Industr Loft 5min Shadyside East Liberty Oakland 6

9.89.8 out of 10 rating
Exceptional
(37 reviews)
Industr Loft 5min Shadyside East Liberty Oakland 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$3,267
NZ$3,267
NZ$467 per night
includes taxes & fees
Image gallery for Spacious Loft 2 bedroom in N Oakland 400, sleeps 8

9.69.6 out of 10 rating
Exceptional
(30 reviews)
Spacious Loft 2 bedroom in N Oakland 400, sleeps 8
Pittsburgh, Pennsylvania
10% off
Price is NZ$5,204
NZ$5,204
NZ$743 per night
includes taxes & fees
Image gallery for Industrial Loft 3 min to Hillman Cancer Center Sleeps 6

1010 out of 10 rating
Exceptional
(31 reviews)
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
Pittsburgh, Pennsylvania
9% off
Price is NZ$3,204
NZ$3,204
NZ$458 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Shadyside
Shadyside Penthouse
Sleeps 10 · 4 bedrooms · 4 bathrooms
7.47.4 out of 10
Goodgood
9 reviews(9 reviews)
4 br 2 baClassical Victorian Home Off Walnut Street in Shadyside Pittsburgh
Sleeps 12 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Walk to Walnut St: Pet-Friendly Pittsburgh Home!
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
💛Shadyside Lodge - Cozy Two BR Getaway💛
Sleeps 8 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Walk to Walnut St: ‘Shadyside House’ w/ Deck
Sleeps 8 · 2 bedrooms · 2 bathrooms
8.68.6 out of 10
Excellentexcellent
9 reviews(9 reviews)
Industrial Loft 3 min to Hillman Cancer Center Sleeps 6
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Top rated rentals - Shadyside
Wonderful time
1010 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore 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.