Cheswick Holiday Rentals

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Holiday Rentals in Cheswick

Stay Pittsburgh
2.0 star property
7.4 out of 10, Good, (46)
"For having 6 kids this was perfect. Walked to the concert at PPG. Great price! "
The price is NZ$236
includes taxes & fees
3 Jun - 4 Jun
Stay Pittsburgh
Abode Pittsburgh - Downtown Convention Center
3.5 star property
7.0 out of 10, Good, (55)
"At night the property was very quiet, and the people that we encountered were very friendly👍"
The price is NZ$317
includes taxes & fees
3 Jun - 4 Jun
Abode Pittsburgh - Downtown Convention Center
Kasa South Side Pittsburgh
4.0 star property
8.8 out of 10, Excellent, (56)
"Much more like a home than a hotel room!"
Kasa South Side Pittsburgh
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The Elliott Hotel at Highland Park
5.0 star property
5.2 out of 10, (9)
"Beautiful vintage property that has been updated and close to everything but still very quiet and private! "
The price is NZ$475
includes taxes & fees
30 May - 31 May
The Elliott Hotel at Highland Park
CozySuites at First Avenue
3.0 star property
8.0 out of 10, Very good, (6)
"Clean, good communication, convenient location and parking! Would book again!"
CozySuites at First Avenue
The Warhola Bloomfield
4.5 star property
6.0 out of 10, (6)
"It was so wonderful I felt like staying at home. The community was beautiful. The atmosphere was great easy to go to any places in the city to go eat dance drink didn’t take long to get there just overall wonderful."
The price is NZ$267
includes taxes & fees
9 Jun - 10 Jun
The Warhola Bloomfield
Luxe Highland Park Apt | The Elliott Mansion
7.2 out of 10, Good, (11)
"We enjoyed our stay!"
The price is NZ$207
includes taxes & fees
30 May - 31 May
Luxe Highland Park Apt | The Elliott Mansion
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
9.6 out of 10, Exceptional, (121)
"Our stay was to help our son who is moving to the area with home renovations. We didn't spend much time at the house other than coming home at the end of the day and cleaning up. It was nice that we could bring our dog, and we felt comfortable in the space with him. The weather was rainy, but the back porch looked like a great space to hang out if it had been nicer."
Cottage near Pittsburgh - Pet Friendly, No Pet/Cleaning Fees, Secluded & Quiet
Spacious Downtown Loft | Free Parking | Gym
10.0 out of 10, Exceptional, (3)
"Overall, I had a wonderful stay. I plan to rent from this renter the next time I am in town. This is just an FYI if my issue happens to someone else. Please contact the renter right away with any issues. The only issue was the 1st night I arrived at 11:30 pm. The orginal apartment that I rented wasn't cleaned. I emailed the renter and received a new apartment within 6 minutes. I was happy with the quick speed of response time and ability to move me to a different apartment considering...
The price is NZ$418
includes taxes & fees
30 May - 31 May
Spacious Downtown Loft | Free Parking | Gym
CozySuites Downtown Pittsburgh
3.5 star property
CozySuites Downtown Pittsburgh
Apartment on the Park
10.0 out of 10, Exceptional, (55)
"It was a wonderful weekend stay! The bed was super comfy my favorite part!"
The price is NZ$153
includes taxes & fees
5 Jun - 6 Jun
Apartment on the Park
Shadyside Penthouse
10.0 out of 10, Exceptional, (1)
"If you have a big family this property is wonderful. The owner is easy to get a hold of an very nice. I highly recommend this property"
Shadyside Penthouse
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
10.0 out of 10, Exceptional, (24)
"Very impressive property: the building is in a nice location with safe entry and car valet, well maintained unit with great views, and friendly responsive host."
🌟 NEW DTWN🌟Three Rivers Luxury Sunset 🌇 Loft
2 King Beds / Free Parking / Arcade / Patio
9.8 out of 10, Exceptional, (9)
"Hi"
The price is NZ$526
includes taxes & fees
18 Jun - 19 Jun
2 King Beds / Free Parking / Arcade / Patio
Modern Meditation 2 Bedroom Apartment
9.4 out of 10, Exceptional, (9)
"It was a pleasant stay. The place was very nice. Was much better than staying in a hotel."
Modern Meditation 2 Bedroom Apartment
424-Apt. 403
3.5 star property
9.6 out of 10, Exceptional, (11)
"WOW! A unique and beautiful apartment. Parking garage was a little bit up the street from the building but convenient with not much street parking. My only complaint was upon arrival and trying to depart someone actually parked right in front of the main entrance making it very tough to unload and load our vehicle. We enjoyed our stay so much that we are talking about when we can return!!"
The price is NZ$314
includes taxes & fees
30 May - 31 May
424-Apt. 403
🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙
9.6 out of 10, Exceptional, (27)
"Beautiful overlook of Pittsburgh, nice neighborhood, clean spacious apartment."
The price is NZ$392
includes taxes & fees
10 Jun - 11 Jun
🏰Warren Castle🏰 - Breathtaking Views of Pittsburgh 💙
Breathtaking Spacious PGH Skyline Loft On Carson Street
8.6 out of 10, Excellent, (17)
"The property was great! The top patio was excellent. Spent a lot of time up there. Beautiful view of city and surrounding area. Easy Uber to penguins game. Right there in the middle of the Carson Street entertainment."
Breathtaking Spacious PGH Skyline Loft On Carson Street
424-Apt 304
3.5 star property
8.8 out of 10, Excellent, (8)
"This place was really cute! There's even access to a private garage for $20/night. My only slight criticism is the beds could be more comfortable with a soft mattress topper and 4 full size pillows per queen bed"
The price is NZ$327
includes taxes & fees
30 May - 31 May
424-Apt 304
Convenient and Cozy Two Bedroom Townhouse
8.6 out of 10, Excellent, (12)
"This was my first time staying at this property and I will definitely rent here again! The communication was amazing and I loved the fact that the owner sent me the nicest email the day of my check in with all the information I needed and restaurant recommendations. This house has everything you need and was so clean. The neighborhood was quiet and the person next door was very nice! Highly recommend!"
Convenient and Cozy Two Bedroom Townhouse
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See all available properties in Cheswick
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.

Other types of properties in Cheswick you may be interested in

Wyndham Grand Pittsburgh Downtown
3.5 star property
7.6 out of 10, Good, (2725)
"The convenience to PNC park was wonderful. The breakfast buffet is good but a little expensive. There are plenty of places to eat around the area. "
The price is NZ$267
includes taxes & fees
30 May - 31 May
Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel
4.0 star property
9.0 out of 10, Wonderful, (1326)
"Beautiful Hotel"
The price is NZ$361
includes taxes & fees
19 Jun - 20 Jun
Omni William Penn Hotel
La Quinta Inn by Wyndham Pittsburgh Airport
2.5 star property
8.0 out of 10, Very good, (1526)
"Room was clean. No bugs. Restaurants near by. Breakfast wasn’t great but not terrible. The only problem was parking. Not enough spaces."
The price is NZ$148
includes taxes & fees
17 Jun - 18 Jun
La Quinta Inn by Wyndham Pittsburgh Airport
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.

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 Cheswick 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 Cheswick. 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 Cheswick. Seeing all the best attractions is bound to make you fall in love with Cheswick. 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 Cheswick short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Cheswick?

Yes, there are holiday rentals close to the most popular sights in Cheswick, 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 Cheswick has to offer?

Shadyside Penthouse: This holiday home rental outside of Cheswick has air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Cheswick?

Allegheny River and Deer Lakes Park are a couple of lovely local spots to get outside and enjoy nature. Other popular places to visit in the area include PPG Paints Arena and PNC Park.

What are holiday rentals like in Cheswick?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cheswick. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.

Recent reviews of Cheswick properties
Expedia verified reviews