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Holiday houses in Penn Hills

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Top-rated holiday rentals in Penn Hills

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Monroeville

4.81 out of 5 average rating, 185 reviews

Pittsburgh Hideaway - Pets - Private

-Discounts on weekly and monthly stays - Put in dates for prices. -1 bedroom house with 1 bath and everything you need for a comfortable stay. -House is tucked away, but also close to the highway and turnpike. -Walking distance to UPMC East, 6 minutes to Forbes Hospital, and min from major shopping/restaurants. -Pet friendly with a large yard (no fence). -Dog park only 7 minutes away - Monroeville Dog Park. Boyce Park and Penn Hills (fenced dog parks) 15 min away -TV- Amazon Stick to login

29 Dec – 5 Jan

$289 NZD per night

Home in Verona

4.87 out of 5 average rating, 247 reviews

Wyckoff-Mason Log House 1774 Historic Landmark

Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

29 Apr – 6 May

$193 NZD per night

Guest favourite

Guest suite in Pittsburgh

4.97 out of 5 average rating, 139 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

5–10 Sep

$174 NZD per night

Guest favourite

Apartment in Pittsburgh

4.95 out of 5 average rating, 387 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

7–14 Jan

$159 NZD per night

Guest favourite

Guest suite in Gibsonia

4.94 out of 5 average rating, 140 reviews

Cozy Comfortable Retreat #1

Beautiful basement guest suite with a gas fireplace, full bath, kitchen with cooktop stove, mini refrigerator and microwave/convection oven. Enjoy off street parking in a quiet friendly neighborhood with outdoor patio. Close to shopping, restaurants, North Park and Hartwood Acres. Downtown Pittsburgh is less than 13 miles away which allows for easy access to all the sporting events Steeler games, Pirate games and Penguin games. Located less than 2 miles from the PA turnpike exit.

28 Jul – 4 Aug

$195 NZD per night

Guest favourite

Apartment in Pittsburgh

4.91 out of 5 average rating, 327 reviews

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

17–24 Feb

$182 NZD per night

Guest favourite

Apartment in Glenshaw

4.95 out of 5 average rating, 195 reviews

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

11–18 Sep

$159 NZD per night

Guest favourite

Home in Irwin

5.0 out of 5 average rating, 108 reviews

Our cozy contemporary home near PA turnpike

Enjoy this peaceful, private residence conveniently located <5 miles from PA turnpike exit 67 with quick access to many restaurants and retail establishments. This is a nicely appointed and recently renovated ranch home in a residential neighborhood with a peaceful outdoor space. There is an open concept living room, dining area and new modern kitchen with stainless steel appliances. The bedrooms have comfortable beds with down comforters .

19–26 Nov

$219 NZD per night

Guest favourite

Townhouse in Pittsburgh

4.92 out of 5 average rating, 120 reviews

Family friendly *garage parking *10 min DT Pitt

Nestled in a quiet neighborhood, our home is the perfect haven for families looking to explore the vibrant city of Pittsburgh. With ample space for everyone to spread out and relax, our home offers a comfortable and inviting atmosphere. We offer premium amenities, including whole bean coffee, tea selection, soft towels, toiletries, and in-unit laundry (w/d) with laundry supplies provided.

9–16 Mar

$326 NZD per night

Guest favourite

Guest suite in Pittsburgh

4.94 out of 5 average rating, 198 reviews

Sweet Mid-Century Modern Suite/Attached Garage

Half-above ground basement studio with secured garage parking (keyless entry) in quiet, peaceful, "Mr. Rogers" neighborhood. Mid-century comfort with modern amenities and eclectic furnishings. Private bath and kitchenette. New queen-size bed, new shower, and new three-quarter sofa bed. Comfortable for single, couple, and 1-2 children. Ground level patio. No stairs or steps.

13–20 Jul

$198 NZD per night

Guest favourite

Cottage in Glenshaw

4.93 out of 5 average rating, 386 reviews

Glenshaw Guesthouse

A one bedroom cottage, on the historic grounds of Glenshaw's "Shaw House". The guesthouse was built on the foundation of a 200-year-old farm shed, nestled against a wooded hillside. Convenient free parking with lots of foliage and privacy. The space feels like it is in the country, but is a short 8 miles from downtown Pittsburgh.

26 Aug – 2 Sep

$290 NZD per night

Townhouse in Pittsburgh

4.83 out of 5 average rating, 156 reviews

Colorful Home Regent Square | 2 King beds + Daybed

Relax with the whole family at this peaceful place to stay. Space for 5 with a fully stocked Chefs kitchen! Enjoy convenient espresso with a Breville espresso machine! Enjoy the large pit couch in the living room for games or to watch a movie! We provide complimentary Prime Video! This space is ready for your pittsburgh getaway!

26 Apr – 3 May

$284 NZD per night

Holiday rentals for every style

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Popular amenities for Penn Hills holiday rentals

Free parking on premises

Air conditioning

Stay near Penn Hills's top sights

Waterworks Shopping Plaza15 locals recommend

Udipi Cafe5 locals recommend

The Lot at Edgewater6 locals recommend

Salvatore's Pizza House3 locals recommend

Carnivores11 locals recommend

The Pub at 3335 locals recommend

Other great holiday rentals in Penn Hills

Guest favourite

Guest suite in Oakmont

4.79 out of 5 average rating, 87 reviews

Cozy one bedroom suite

12–19 Jan

$198 NZD per night

Guest favourite

Home in Pittsburgh

4.93 out of 5 average rating, 14 reviews

relax enjoy and be happy

6–13 Nov

$184 NZD per night

Apartment in Springdale

4.79 out of 5 average rating, 42 reviews

2br gem in cute small town.

12–19 Sep

$204 NZD per night

Guest favourite

Home in Verona

4.86 out of 5 average rating, 49 reviews

Neighborhood Charmer

29 May – 5 Jun

$253 NZD per night

Guest favourite

Apartment in Aspinwall

4.97 out of 5 average rating, 35 reviews

Aspinwall 1 bedroom Apartment

30 Nov – 7 Dec

$251 NZD per night

Guest favourite

Home in Monroeville

4.83 out of 5 average rating, 60 reviews

3 Bedroom Pittsburgh Neighbor - Pets

8–15 Mar

$256 NZD per night

Guest favourite

Guesthouse in Pittsburgh

4.95 out of 5 average rating, 39 reviews

Unique Rustic Carriage House

4–11 Jan

$259 NZD per night

Guest favourite

Apartment in Pittsburgh

5.0 out of 5 average rating, 7 reviews

Upscale King Suite by WholeFoods

11–18 Dec

$212 NZD per night

Quick stats about holiday rentals in Penn Hills

Total rentals
120 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.9K reviews
Nightly prices starting at
$34 NZD before taxes and fees

Destinations to explore