Vacation rentals in Penn Hills

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Top-rated vacation rentals in Penn Hills

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

Superhost

Home in Monroeville

4.8 out of 5 average rating, 184 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

May 23 – 30

G$22,277 GYD per night
Superhost

Home in Verona

4.87 out of 5 average rating, 243 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.

Jun 2 – 9

G$20,967 GYD per night
Guest favorite

Guest suite in Pittsburgh

4.95 out of 5 average rating, 230 reviews

Warm & Cozy, Newly Remodeled Private Space.

The PITT Stop Explore Pittsburgh’s vibrant streets with this warm & cozy, newly remodeled studio as your base! The PITT Stop is centrally located in Brighton Heights, a smaller section of Pittsburgh’s North Side. One of the most historic and culturally eclectic areas you will find. Here in Brighton Heights, you’ll be rooted in the coziness of an urban neighborhood while being close to everything metropolitan Pittsburgh has to offer. **Please see ‘Other Details to Note’ section for more.**

Dec 25 – Jan 1

G$19,337 GYD per night

Popular amenities for Penn Hills vacation rentals

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 vacation rentals in Penn Hills

Guest favorite

Home in Pittsburgh

4.93 out of 5 average rating, 259 reviews

Upscale Modern 2 BR Apartment

Sep 9 – 16

G$27,092 GYD per night
Guest favorite

Home in Irwin

5.0 out of 5 average rating, 106 reviews

Our cozy contemporary home near PA turnpike

Nov 23 – 30

G$22,633 GYD per night
Guest favorite

Home in Verona

4.85 out of 5 average rating, 47 reviews

Neighborhood Charmer

Sep 25 – Oct 2

G$23,091 GYD per night
Superhost

Apartment in Springdale

4.81 out of 5 average rating, 72 reviews

Vibey 1BDR apartment for rent in charming town.

Nov 12 – 19

G$15,589 GYD per night
Superhost

Apartment in Pittsburgh

4.93 out of 5 average rating, 15 reviews

#43 Cozy Suite - Marina River view near Oakmont

Jan 11 – 18

G$27,906 GYD per night
Superhost

Apartment in Springdale

4.79 out of 5 average rating, 39 reviews

2br gem in cute small town.

Aug 30 – Sep 6

G$20,598 GYD per night
Guest favorite

Apartment in Aspinwall

4.97 out of 5 average rating, 33 reviews

Aspinwall 1 bedroom Apartment

Dec 23 – 30

G$25,048 GYD per night
Guest favorite

Guest suite in Oakmont

4.79 out of 5 average rating, 86 reviews

Cozy one bedroom suite

Oct 23 – 30

G$21,505 GYD per night
Guest favorite

Guesthouse in Pittsburgh

4.95 out of 5 average rating, 38 reviews

Unique Rustic Carriage House

Aug 17 – 24

G$26,714 GYD per night
Guest favorite

Home in Pittsburgh

5.0 out of 5 average rating, 11 reviews

Cozy three bedroom home close to shopping and more

Feb 5 – 12

G$43,448 GYD per night
Guest favorite

Apartment in Monroeville

4.88 out of 5 average rating, 17 reviews

PGH's Charming Suburban Oasis

Jan 28 – Feb 4

G$30,036 GYD per night
Superhost

Home in Murrysville

4.9 out of 5 average rating, 59 reviews

Gorgeous Modernized Cabin + Hot Tub + Pool Table

Feb 5 – 12

G$65,206 GYD per night

Quick stats about vacation rentals in Penn Hills

Total rentals

120 properties

Rentals with dedicated workspaces

70 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

3.5K reviews

Nightly prices starting at

G$4,188 GYD before taxes and fees

Frequently Asked Questions

  • Do house rentals in Penn Hills have air conditioning?

    Absolutely! We offer over 60 house rentals with air conditioning in Penn Hills. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Penn Hills?

    Penn Hills has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Penn Hills have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Penn Hills. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Penn Hills have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Penn Hills. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Bed And Breakfast Rentals in Penn Hills?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Penn Hills?

    Yes! Work meets play with ease at over 70 vacation rentals in Penn Hills featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do apartment rentals in Penn Hills have a kitchen?

    Absolutely! We offer over 20 apartment rentals with a kitchen in Penn Hills. Enjoy a tailored experience with all the comforts you desire.

  • Where should I stay in Penn Hills?

    Make yourself at home in Penn Hills by choosing from our most frequently booked neighborhoods. We have over 250 vacation rentals in Dark Hollow Road, over 220 vacation rentals in Edgewater, and over 250 vacation rentals in Upper Oakmont.

  • Are there pet-friendly vacation rentals in Penn Hills?

    Four-legged friends are welcome in Penn Hills. Choose from more than 30 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in bed and breakfast rentals in Penn Hills?

    Experience the best of Penn Hills with our bed and breakfast rentals, starting at about $350 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore