Cheswick Holiday Rentals

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Check prices for these dates

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Cheswick holiday rentals

Property grounds
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions

Holiday Home in Cheswick

Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions
2.0 star property
8.4 out of 10, Very good, (9)
"This is one of my favorite locations I’ve stayed at. The house is lovely, clean, comfortable, quiet, has everything you need, the pool and hot tub are fantastic, and it’s close to anywhere you want to go while feeling like a hideaway retreat. I’m already looking forward to coming back! "
United States
Criss V.
The price is HK$1,945
HK$3,479 total
includes taxes & fees
31 Jan - 1 Feb 2026
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions
Interior
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!

Cottage in Mount Washington

Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
3.0 star property
9.4 out of 10, Exceptional, (3)
"Perfect for our needs"
United States
Barbara
The price is HK$459
HK$2,447 total
includes taxes & fees
6 Jan - 7 Jan 2026
Dog-friendly Pittsburgh Home, 3 Mi to Downtown!
Dining
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen

Apartment in Squirrel Hill

3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
2.0 star property
10.0 out of 10, Exceptional, (3)
"It was a pleasure staying there"
United States
msimchowitz
The price is HK$447
HK$1,740 total
includes taxes & fees
1 Jan - 2 Jan 2026
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
Fridge, microwave, oven, stovetop
Cozy&Modern 2 Bdr Apt Natrona

Apartment in Natrona Heights

Cozy&Modern 2 Bdr Apt Natrona
2.0 star property
9.6 out of 10, Exceptional, (10)
"Great property, very cozy and clean. Easy access to Rte 28 and into Pittsburgh."
United States
Darren H.
The price is HK$817
HK$1,098 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy&Modern 2 Bdr Apt Natrona
Terrace/patio
Hungry Hollow Hideaway - Luxury Cabin on Private Acreage

Cabin in Vandergrift

Hungry Hollow Hideaway - Luxury Cabin on Private Acreage
2.0 star property
10.0 out of 10, Exceptional, (5)
The price is HK$1,835
HK$2,660 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hungry Hollow Hideaway - Luxury Cabin on Private Acreage
Fridge, microwave, oven, stovetop
Spacious 1-Bedroom Apartment In Pittsburgh (B1)

Apartment in Friendship

Spacious 1-Bedroom Apartment In Pittsburgh (B1)
9.6 out of 10, Exceptional, (37)
"This was a perfect place to stay for a week, exactly as advertised, no issues. Nice area. Very private space."
United States
Sally R.
The price is HK$544
HK$1,496 total
includes taxes & fees
25 Jan - 26 Jan 2026
Spacious 1-Bedroom Apartment In Pittsburgh (B1)
Interior
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home

Mobile Home in Lawrenceville

★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home
10.0 out of 10, Exceptional, (4)
"Great location! Very clean, street is super quiet"
United States
Daryll J.
The price is HK$522
HK$1,338 total
includes taxes & fees
1 Jan - 2 Jan 2026
★ HostWise Stays ★ Le Petit Riad: A Moroccan Oasis Tiny Home
Free WiFi
461 Melwood Suites Unit 102 Studio

Apartment in Oakland

461 Melwood Suites Unit 102 Studio
2.0 star property
10.0 out of 10, Exceptional, (2)
"Property manage me were very responsive. We added one more night close to our stay because we realize our flight was arriving super early, so we reached out, problem solved. Also, we got good recommendations on what’s around the area to eat and local sight seeing places not promoted on the internet. Overall, best customer services all around"
United States
Steve
The price is HK$840
HK$2,123 total
includes taxes & fees
4 Jan - 5 Jan 2026
461 Melwood Suites Unit 102 Studio
Dining
Beautiful 3BR Home with Cozy Front & Back Porches!

Holiday Home in Munhall

Beautiful 3BR Home with Cozy Front & Back Porches!
9.4 out of 10, Exceptional, (28)
"Clean property, easy access to The Waterfront. The Host was very responsive and helpful. 10/10 would recommend. "
United States
Phillip M.
The price is HK$707
HK$1,672 total
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful 3BR Home with Cozy Front & Back Porches!
Fridge, microwave, oven, stovetop
Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg

Apartment in Lawrenceville

Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg
9.0 out of 10, Wonderful, (8)
"Place as decribed. Would stay again"
United States
Ryan W.
Bloomfield/Pittsburgh Bright & Spacious 2BD w/Prkg
Fridge, microwave, oven, stovetop
★ HostWise Stays ★ 4 Blocks From UPMC Children's

Holiday Home in Lawrenceville

★ HostWise Stays ★ 4 Blocks From UPMC Children's
10.0 out of 10, Exceptional, (14)
"Great location and communication from host! The home was clean, comfortable, and exactly as described. We loved and appreciated the kitchen amenities! We very much enjoyed our stay. We would absolutely stay here again and highly recommend this rental. "
United States
Heather S.
The price is HK$576
HK$1,523 total
includes taxes & fees
20 Jan - 21 Jan 2026
★ HostWise Stays ★ 4 Blocks From UPMC Children's
Front of property
424-Apt 304

Apartment in Oakland

424-Apt 304
3.5 star property
9.2 out of 10, Wonderful, (12)
"Love the location nicely done Will return "
United States
Lamont
The price is HK$840
HK$1,445 total
includes taxes & fees
12 Jan - 13 Jan 2026
424-Apt 304
1 bedroom, desk, iron/ironing board, travel cot
*New* Loft 5 min Shadyside/East Liberty Sleeps 4

Apartment in Oakland

*New* Loft 5 min Shadyside/East Liberty Sleeps 4
2.0 star property
9.4 out of 10, Exceptional, (6)
"Very nice, modern and clean room!"
United States
Kimberly S.
The price is HK$715
HK$1,292 total
includes taxes & fees
1 Jan - 2 Jan 2026
*New* Loft 5 min Shadyside/East Liberty Sleeps 4
Interior
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

Holiday Home in Bloomfield

1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
10.0 out of 10, Exceptional, (27)
"Nice place. Came exactly as advertised. Nice diverse neighborhood with a lot available within walking distance."
United States
Gary L.
The price is HK$505
HK$1,451 total
includes taxes & fees
25 Jan - 26 Jan 2026
1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area
1 bedroom, free WiFi, bed sheets
Butler's heart!

Apartment in Lawrenceville

Butler's heart!
9.0 out of 10, Wonderful, (26)
"Beautiful, cozy, and clean! Loved this place and would definitely stay here again. Great location and not too far away from the downtown. "
United States
Jose V.
The price is HK$420
HK$1,221 total
includes taxes & fees
7 Jan - 8 Jan 2026
Butler's heart!
Fridge, microwave, oven, stovetop
Brand New ★ Prime Location ★ Exposed Brick Beauty!

Holiday Home in Lawrenceville

Brand New ★ Prime Location ★ Exposed Brick Beauty!
10.0 out of 10, Exceptional, (22)
"Wonderful space right in Lawrenceville, easy access to downtown Pittsburgh. We had a great time and would stay again!"
United States
Alex S.
The price is HK$682
HK$1,608 total
includes taxes & fees
15 Jan - 16 Jan 2026
Brand New ★ Prime Location ★ Exposed Brick Beauty!
Terrace/patio
Explore Pittsburgh from a Modern, Hip Bungalow

Holiday Home in North Side

Explore Pittsburgh from a Modern, Hip Bungalow
9.6 out of 10, Exceptional, (56)
"Very easy to get to off of the highway. Nice and cozy home with all the necessities you should need. Lovely welcome committee out front to say hello. The place was clean and nicely organized."
United States
Kathleen C.
The price is HK$476
HK$1,373 total
includes taxes & fees
1 Jan - 2 Jan 2026
Explore Pittsburgh from a Modern, Hip Bungalow
Interior
Abode Pittsburgh - Downtown Convention Center

Apartment in Downtown Pittsburgh

Abode Pittsburgh - Downtown Convention Center
3.5 star property
7.6 out of 10, Good, (87)
"Good location, clean place. Was affordable. Perfect for our guys weekend, with the 3 of us. "
United States
Michael
The price is HK$399
HK$1,243 total
includes taxes & fees
6 Jan - 7 Jan 2026
Abode Pittsburgh - Downtown Convention Center
Property grounds
Urban Retreat with Garage on Mt. Washington

Holiday Home in Mount Washington

Urban Retreat with Garage on Mt. Washington
10.0 out of 10, Exceptional, (69)
"It’s was amazing and accommodating and I loved it!"
United States
Lindsy M.
The price is HK$536
HK$1,354 total
includes taxes & fees
6 Jan - 7 Jan 2026
Urban Retreat with Garage on Mt. Washington
Terrace/patio
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Holiday Home in Plum

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
10.0 out of 10, Exceptional, (14)
"Easy check in! Shelly was wonderful to communicate with and thorough! We had a great stay! There were even some snack she left and coffee which came in handy! Definite recommend staying there!"
United States
Melissa M.
The price is HK$1,322
HK$2,288 total
includes taxes & fees
2 Jan - 3 Jan 2026
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
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 Cheswick Hotel Reviews

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

10/10 Excellent
"Wonderful hotel. "
Dawn 2-night trip
Posted 20 hours ago
The Landing Hotel at Rivers Casino

Find out more about Cheswick

Search for holiday rentals in Cheswick on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheswick using one of the methods below:

  • View our selection of featured holiday rentals in Cheswick
  • Use the map to find apartments and other holiday homes in the Cheswick neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheswick while they last

Look no further and take a look at our great range of rental properties in Cheswick!

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?

Not so tiny house with full kitchen & patio swing: This holiday home rental outside of Cheswick is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Cheswick?

Expedia has 3 holiday rentals for your stay in Cheswick.

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. In the wider area, you’ll find PNC Park and Oakmont Country Club.

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.