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Penn Holiday Rentals

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Our top choices for Penn holiday rentals

1. Tranquility surrounds this house. View includes Three Lakes & Quiet wilderness.

Tranquility surrounds this house. View includes Three Lakes & Quiet wilderness.
Jeannette
10.0 out of 10, Exceptional, (1 review)
"Nancy was an incredible host. Everyone at the property was so wonderful, welcoming, and helpful. We had everything we needed in the most beautiful, peaceful place."
United States
Jen U.
The price is NZ$388
includes taxes & fees
17 Sept - 18 Sept
Tranquility surrounds this house. View includes Three Lakes & Quiet wilderness.

2. Walk to BTV Winery | Near Corporate Offices

Walk to BTV Winery | Near Corporate Offices
Hunker
10.0 out of 10, Exceptional, (14 reviews)
"Everything was wonderful - very clean, very cozy! We enjoyed our stay very much!"
United States
Kate R.
The price is NZ$477
includes taxes & fees
30 Aug - 31 Aug
Walk to BTV Winery | Near Corporate Offices

3. The Upper Room

The Upper Room
McKeesport
9.6 out of 10, Exceptional, (13 reviews)
"Great place and an awesome host!"
United States
John B.
The price is NZ$331
includes taxes & fees
7 Sept - 8 Sept
The Upper Room

4. The Light Room

The Light Room
McKeesport
8.4 out of 10, Very good, (17 reviews)
"Loved it here "
United States
Ciara S.
The price is NZ$321
includes taxes & fees
31 Aug - 1 Sept
The Light Room

5. Charming 3-bedroom townhome with AC and WiFi in Greensburg

Charming 3-bedroom townhome with AC and WiFi in Greensburg
Greensburg
9.2 out of 10, Wonderful, (11 reviews)
"Great place to stay. Centrally located"
United States
Randall M.
The price is NZ$569
includes taxes & fees
7 Sept - 8 Sept
Charming 3-bedroom townhome with AC and WiFi in Greensburg

6. 3bd home in Mt. Pleasant; near festivals, biking, skiing.

3bd home in Mt. Pleasant; near festivals, biking, skiing.
Mount Pleasant
10.0 out of 10, Exceptional, (13 reviews)
"Such a wonderful and kind host. Great communication from start to finish. Quiet area. My kiddos loved the toys and felt right at home. Thank you for a great stay! "
United States
Jessica H.
The price is NZ$371
includes taxes & fees
30 Aug - 31 Aug
3bd home in Mt. Pleasant; near festivals, biking, skiing.

7. Charming 3-bedroom house in soothing West Newton neighborhood

Charming 3-bedroom house in soothing West Newton neighborhood
West Newton
10.0 out of 10, Exceptional, (4 reviews)
"We enjoyed our stay a lot ! Beautiful home ."
United States
Sara R.
The price is NZ$445
includes taxes & fees
2 Sept - 3 Sept
Charming 3-bedroom house in soothing West Newton neighborhood

8. Penn Hills Home ~ 11 Mi to Pittsburgh

Penn Hills Home ~ 11 Mi to Pittsburgh
Penn Hills
9.0 out of 10, Wonderful, (7 reviews)
"Clean property, easy check in process, Accessible and supportive host"
United States
Nara S.
The price is NZ$642
includes taxes & fees
1 Sept - 2 Sept
Penn Hills Home ~ 11 Mi to Pittsburgh

9. Crow's Nest Crash-Pad

Crow's Nest Crash-Pad
Homestead
7.6 out of 10, Good, (14 reviews)
"I was weary to book because of some of the other reviews, however it was a great place to stay! It was such a cute and cozy little place! It was also very clean when we got there! You definitely get your moneys worth and more. Will for sure be back next time I’m in town!"
United States
Destinee F.
The price is NZ$270
includes taxes & fees
13 Sept - 14 Sept
Crow's Nest Crash-Pad

10. Penn Hills Home ~ 11 Mi to Pittsburgh

Penn Hills Home ~ 11 Mi to Pittsburgh
3.0 star property
Penn Hills
The price is NZ$636
includes taxes & fees
30 Aug - 31 Aug
Penn Hills Home ~ 11 Mi to Pittsburgh

11. 3min>Walnut:UPMC Shadyside:3min>CMU:Full Kitchen

3min>Walnut:UPMC Shadyside:3min>CMU:Full Kitchen
Squirrel Hill
9.6 out of 10, Exceptional, (4 reviews)
"Great apartment…wonderful location!"
United States
Michael L.
The price is NZ$344
includes taxes & fees
1 Sept - 2 Sept
3min>Walnut:UPMC Shadyside:3min>CMU:Full Kitchen

12. Secluded Chalet near Ohiopyle and Seven Springs

Secluded Chalet near Ohiopyle and Seven Springs
Bear Rocks
10.0 out of 10, Exceptional, (3 reviews)
"Mike was great. Place is as advertised. Worked well for our weekend at Seven Springs. "
United States
Ryan C.
The price is NZ$417
includes taxes & fees
3 Sept - 4 Sept
Secluded Chalet near Ohiopyle and Seven Springs

13. Melwood Suites Unit 107 Studio

Melwood Suites Unit 107 Studio
2.0 star property
Oakland
9.6 out of 10, Exceptional, (47 reviews)
"Exceptionally clean, spacious, very comfortable!"
United States
Lisa
The price is NZ$192
includes taxes & fees
9 Sept - 10 Sept
Melwood Suites Unit 107 Studio

14. Hydee's Hideaway

Hydee's Hideaway
Swissvale
10.0 out of 10, Exceptional, (36 reviews)
"The location was great and the property owners were kind and helped us during our stay. "
United States
Cathy K.
The price is NZ$599
includes taxes & fees
1 Sept - 2 Sept
Hydee's Hideaway

15. Stylish House near Frick Park

Stylish House near Frick Park
Squirrel Hill South
9.8 out of 10, Exceptional, (10 reviews)
"Cozy house, had everything we needed in a very convenient location."
United States
Warren S.
The price is NZ$379
includes taxes & fees
31 Aug - 1 Sept
Stylish House near Frick Park

16. Shadyside/Pittsburgh, Modern & Unique 1 Bedroom with Free Parking

Shadyside/Pittsburgh, Modern & Unique 1 Bedroom with Free Parking
Shadyside
9.2 out of 10, Wonderful, (10 reviews)
"Lovely place, good location. Would stay again!"
United States
Nicole B.
Shadyside/Pittsburgh, Modern & Unique 1 Bedroom with Free Parking

17. Off Street Reserved Parking, Full Kitchen, Newly Renovated

Off Street Reserved Parking, Full Kitchen, Newly Renovated
Verona
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was very cute, well outfitted, and conveniently located in downtown Verona. I will stay here again! The hosts were responsive and helpful."
United States
Ann B.
Off Street Reserved Parking, Full Kitchen, Newly Renovated

18. Spacious 1-Bedroom Apartment In Pittsburgh (B1)

Spacious 1-Bedroom Apartment In Pittsburgh (B1)
Friendship
9.6 out of 10, Exceptional, (43 reviews)
"Located in a quiet neighborhood with street parking. Shops nearby. Clean and comfortable. Could use additional plates and coffee mugs. Overall a nice stay."
United States
Deborah A.
The price is NZ$308
includes taxes & fees
2 Sept - 3 Sept
Spacious 1-Bedroom Apartment In Pittsburgh (B1)

19. Shadyside/Central @2 Bright and Stylish Studio with Free Parking

Shadyside/Central @2 Bright and Stylish Studio with Free Parking
Shadyside
9.8 out of 10, Exceptional, (9 reviews)
"Great location, close to excellent coffee shops and restaurants. The host was very communicative, and the place was clean and well maintained."
United States
Antonio A.
The price is NZ$218
includes taxes & fees
31 Aug - 1 Sept
Shadyside/Central @2 Bright and Stylish Studio with Free Parking

20. Fire Pit + Family Friendly + Great Location!

Fire Pit + Family Friendly + Great Location!
Bloomfield
9.8 out of 10, Exceptional, (10 reviews)
"The host was very responsive when we had questions and the place was very nice. "
United States
Robyn H.
The price is NZ$448
includes taxes & fees
31 Aug - 1 Sept
Fire Pit + Family Friendly + Great Location!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Penn Hotel Reviews

Find out more about Penn

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Penn holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Penn. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Penn. Seeing all the best attractions is bound to make you fall in love with Penn. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Penn short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Penn?

Yes, there are holiday rentals close to the most popular sights in Penn, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Penn has to offer?

The Light Room: This holiday home rental outside of Penn is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

What’s there to see and do in Penn?

Explore the area and family-friendly sights such as Kennywood, or get out into nature at a spot like Frick Park. Seton Hill University and The Palace Theatre are a couple of places you'll find in the wider area.

What’s a holiday rental in Penn like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Penn. Holiday rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips.