Cheswick Vacation Rentals

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Browse Select Cheswick Vacation Homes

Our top choices for Cheswick vacation homes

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

2.0 star property
8.0 out of 10, Very good, (6)
"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! "
The price is CA $313
CA $578 total
includes taxes & fees
Sep 9 - Sep 10
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions

Chic Studio • City Views • Steps to Hospital

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very close walk/drive to downtown. Plenty of places to eat and visit in the area. "
The price is CA $90
CA $324 total
includes taxes & fees
Aug 25 - Aug 26
Chic Studio • City Views • Steps to Hospital

Pittsburgh History • Eclectic Luxury • Upper Lawrenceville

2.0 star property
10.0 out of 10, Exceptional, (6)
"Gorgeously appointed and all the amenities you need and then some! And we got to actually meet Slim Forsyth who the place is themed around, so fun and pleasant. Very accommodating to our two dogs. Also a great location and walkable to coffee shops, restaurants and boutiques. We would definitely stay here again. "
The price is CA $138
CA $531 total
includes taxes & fees
Aug 27 - Aug 28
Pittsburgh History • Eclectic Luxury • Upper Lawrenceville

Restful Nest near downtown

9.0 out of 10, Wonderful, (6)
"Stayed over after concert and avoided all the traffic. Convenient to Station Square parking and Gateway Clipper. Owner very responsive to messages and questions. Comfortable beds, clean and updated."
The price is CA $156
CA $418 total
includes taxes & fees
Aug 23 - Aug 24
Restful Nest near downtown

Iconic 3BD Entire House in The Heart Of Pittsburg

2.0 star property
The price is CA $202
CA $486 total
includes taxes & fees
Aug 24 - Aug 25
Iconic 3BD Entire House in The Heart Of Pittsburg

Accessible • Family Friendly • Safe Locale

9.8 out of 10, Exceptional, (18)
"Super cute house, lots of street parking, pet friendly. Host was very nice and responsive. Great place to stay!"
The price is CA $165
CA $518 total
includes taxes & fees
Aug 26 - Aug 27
Accessible • Family Friendly • Safe Locale

Yinz Retreat, Above the City Home

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay at, loved the ambiance, the view of the city was amazing. It is spacious, and the top floor is great for adults and kids to just hang out in. Would definitely book again when we come back out here. "
The price is CA $259
CA $730 total
includes taxes & fees
Aug 25 - Aug 26
Yinz Retreat, Above the City Home

BEAUTIFULLY FURNISHED TWO-BEDROOM UNIT, LOADED WITH APPLIANCES AND PARKING

2.0 star property
9.2 out of 10, Wonderful, (5)
"Quick drive to the beach. Great location "
The price is CA $150
CA $373 total
includes taxes & fees
Aug 23 - Aug 24
BEAUTIFULLY FURNISHED TWO-BEDROOM UNIT, LOADED WITH APPLIANCES AND PARKING

The Upper Room

10.0 out of 10, Exceptional, (1)
"House was clean, comfortable, very peaceful, beautiful view of the mountains"
The price is CA $119
CA $229 total
includes taxes & fees
Aug 25 - Aug 26
The Upper Room

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (26)
"got a lil warm in the house the first night but over all a great place"
The price is CA $63
CA $341 total
includes taxes & fees
Aug 25 - Aug 26
❤️Cozy Townhome on Carey with Private Deck Space ❤️

Modern and Spacious House

2.0 star property
8.0 out of 10, Very good, (1)
"The house was cleaned and had lots of space. One bath for the bedrooms, a powder room on the main floor and a shower in the basement with toilet. My grandchild came to visit and enjoyed the swings and bunnies in the yard"
The price is CA $146
CA $459 total
includes taxes & fees
Aug 26 - Aug 27
Modern and Spacious House

Charming 2-bedroom building with fitness room and AC in Clairton

The price is CA $145
CA $242 total
includes taxes & fees
Aug 23 - Aug 24
Charming 2-bedroom building with fitness room and AC in Clairton

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (11)
"Super clean and comfortable. Centrally located. Great for family. Everyone enjoyed their stay."
The price is CA $153
CA $209 total
includes taxes & fees
Aug 25 - Aug 26
Stylish & Central 3BD Home Pittsburgh/North Side

Explore Pittsburgh from a Modern, Hip Bungalow

9.6 out of 10, Exceptional, (49)
"This home is comfortable, nicely furnished, and decorated, clean, and very relaxing. Just what I wanted. "
The price is CA $80
CA $224 total
includes taxes & fees
Aug 28 - Aug 29
Explore Pittsburgh from a Modern, Hip Bungalow

4Bed Steeler w/ BBQ_Firepit_Games_SecretGarden_MoodyVibe_7mile to DTown

8.4 out of 10, Very good, (6)
"Stayed for a weekend to have some drinks and play some games with friends. The space was exactly what we were looking for, 3 bedrooms/4 beds, nice dining and living rooms. The host was incredibly responsive and very accommodating. "
The price is CA $104
CA $396 total
includes taxes & fees
Aug 25 - Aug 26
4Bed Steeler w/ BBQ_Firepit_Games_SecretGarden_MoodyVibe_7mile to DTown

Bright and Spacious Duplex

The price is CA $218
CA $278 total
includes taxes & fees
Aug 25 - Aug 26
Bright and Spacious Duplex

Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking

9.8 out of 10, Exceptional, (7)
"We stayed here to attend a conference in downtown. The apartment description on listing is very accurate, nice and clean with good amenities! Host was very responsive to all our questions. The neighborhood is great and location is walking distance to good cafes and restaurants. The only downside was that the location was not as close to downtown as we expected and public transportation not great and we had to use Uber to get to hotel daily in downtown where conference was which was costly. "
The price is CA $127
CA $178 total
includes taxes & fees
Aug 24 - Aug 25
Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking

★ Amazing Location ★ King Bed ★ Beautiful Space!

9.6 out of 10, Exceptional, (10)
"Property was very clean and well appointed. Close to great restaurants. Would definitely recommend"
The price is CA $182
CA $395 total
includes taxes & fees
Aug 24 - Aug 25
★ Amazing Location ★ King Bed ★ Beautiful Space!

Modern All-New, Near Downtown, Private Parking - walking to Children Hospital

10.0 out of 10, Exceptional, (54)
"Thanks for a great place at a fair price. "
The price is CA $184
CA $497 total
includes taxes & fees
Aug 24 - Aug 25
Modern All-New, Near Downtown, Private Parking - walking to Children Hospital

King Bed | Free Parking | Arcade | Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (24)
"Very nice property. "
The price is CA $167
CA $510 total
includes taxes & fees
Sep 8 - Sep 9
King Bed | Free Parking | Arcade | Fire Pit
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