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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.

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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

Mar 11 – 18

G$21,648 GYD 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.

Feb 2 – 9

G$21,649 GYD per night

Guest suite in Pittsburgh

4.97 out of 5 average rating, 137 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.

Sep 5 – 10

G$18,003 GYD per night

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!

Mar 12 – 19

G$17,229 GYD per night

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.

Sep 15 – 22

G$20,083 GYD per night

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.

Oct 31 – Nov 7

G$19,759 GYD per night

Apartment in Pittsburgh

4.99 out of 5 average rating, 144 reviews

504 Bascom Ave Serene Luxury

Nestled in the middle of an adorable community of stone cottages, this historic structure built in 1938 was the first home John Mattys built in this neighborhood. He went on to build all the houses on Mattys (named after himself) and Oceanas Avenues (named for the sisters that commissioned and lived in this duplex). Re-imagined for contemporary lifestyles, 504 Bascom is your cozy cottage but with all the amenities you deserve. I look forward to hosting you!

Aug 22 – 29

G$24,428 GYD per night

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

Jul 25 – Aug 1

G$16,342 GYD per night

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 .

Dec 4 – 11

G$22,588 GYD per night

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.

Jul 13 – 20

G$21,462 GYD per night

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.

Aug 25 – Sep 1

G$30,984 GYD per night

Apartment in East McKeesport

4.96 out of 5 average rating, 171 reviews

Quiet Luxury Apartment! Floor 2

A large sun filled, luxury apartment. new tile flooring, new cabinets with granite countertop, new bathroom with custom marble. A living room, open kitchen to dining area, 3 bedrooms, one full bathroom and deck. Off street parking for 2 cars. Quiet street, off Route 30 close to main street with bus lines.

Aug 25 – Sep 1

G$30,524 GYD per night

Vacation rentals for every style

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Popular amenities for Penn Hills vacation 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 vacation rentals in Penn Hills

Guest suite in Oakmont

4.79 out of 5 average rating, 87 reviews

Cozy one bedroom suite

Feb 26 – Mar 5

G$21,462 GYD per night

Apartment in Springdale

4.78 out of 5 average rating, 41 reviews

2br gem in cute small town.

May 29 – Jun 5

G$23,633 GYD per night

Apartment in Aspinwall

4.97 out of 5 average rating, 35 reviews

Aspinwall 1 bedroom Apartment

Jan 22 – 29

G$24,997 GYD per night

Guesthouse in Pittsburgh

4.95 out of 5 average rating, 39 reviews

Unique Rustic Carriage House

Aug 14 – 21

G$28,928 GYD per night

Apartment in Pittsburgh

5.0 out of 5 average rating, 7 reviews

Upscale King Suite by WholeFoods

Jan 2 – 9

G$22,048 GYD per night

Home in Duquesne

4.91 out of 5 average rating, 85 reviews

Entire home near Kennywood. No cleaning or pet fee

May 8 – 15

G$24,835 GYD per night

Home in New Kensington

4.98 out of 5 average rating, 64 reviews

Mid-Century Burrell Bungalow

Feb 23 – Mar 2

G$38,417 GYD per night

Apartment in Munhall

4.9 out of 5 average rating, 98 reviews

Comfortable & Cozy Steel Town Apartment!

Mar 17 – 24

G$18,774 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	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	G$4,179 GYD before taxes and fees

Frequently Asked Questions

Do apartment rentals in Penn Hills have air conditioning?
Absolutely! We offer over 20 apartment 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 bed and breakfast rentals in Penn Hills have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Penn Hills. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Penn Hills have wifi?
Absolutely! We offer over 70 house rentals with wifi in Penn Hills. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Penn Hills?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with wifi, over 60 homes with air conditioning, over 60 homes with free parking, over 70 homes with a kitchen, 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 260 vacation rentals in Upper Oakmont, over 220 vacation rentals in Edgewater, and over 260 vacation rentals in Dark Hollow Road.
Are there pet-friendly vacation rentals in Penn Hills?
Four-legged friends are welcome in Penn Hills. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Penn Hills?
Experience the best of Penn Hills with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore