
Holiday rentals in Cheswick
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Top-rated holiday rentals in Cheswick
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Cheswick
Top guest favourite

Home in Pittsburgh
5 out of 5 average rating, 13 reviewsBeautiful 3br/2b family house
SarahRating, 5 stars2 weeks ago
The home is absolutely beautiful and might have actually inspired me to remodel my home decor after theirs. It’s in a peaceful, quiet location, but only a few minutes from a grocery store, which was perfect for us. I would definitely recommend this day for anyone especially for a family setting. My two year-old daughter absolutely loved the play kitchen, and there was definitely enough space for me, my husband and my daughter, along with my parents and my brother to all comfortably fit and spend extra time together while in town for my sister’s wedding.
Top guest favourite

Private room in Pittsburgh
4.98 out of 5 average rating, 568 reviewsBasement apartment with private entrance and bath
KristenRating, 5 stars4 days ago
Michael's place was great, would definitely stay here again. It had everything we needed and more...loved the coffee/tea and snacks...no complaints!
Top guest favourite

Guest suite in Pittsburgh
5 out of 5 average rating, 7 reviewsHidden Oasis-Hot Tub & King Bed
JanieRating, 5 stars2 days ago
My husband and I stayed here for one night and we loved it! Brady was a great host and was flexible with our arrival time. Brady had the hot tub ready for us upon arrival, as well as wood in the outdoor fire place. We spent most of our night outside enjoying the “private oasis.” What a beautiful space! Worth mentioning that the hot tub is covered so you can enjoy it even if it’s raining. This was a perk, as we were worried about rain. Thanks, Brady, for a wonderful experience! You were accommodating and communicative. We highly recommend your space!

Home in Apollo
5 out of 5 average rating, 3 reviewsYew Arbor Cottage
BryanRating, 5 stars8 months ago
It was a great stay. Beautiful yard. Accommodations were all met and more. Everything you need was thought of. Very thoughtful, typed paper explaining things in the area and remembered we were going to a wedding. Overall, great experience.

Home in Harwick
4.69 out of 5 average rating, 13 reviewsQuiet 3 BR Suburban Home Close to Pittsburgh
ZbigniewRating, 5 stars8 months ago
Very clean and as described. Easy to find, parking in the driveway, close to just about everything
Superhost

Private room in Cheswick
4.84 out of 5 average rating, 101 reviewsA private & spacious room in Northeast Pittsburgh
HedwigRating, 5 stars8 months ago
This was my second time that I stayed there. Perfect for my needs! Would go there again if I travel to this area!
Guest favourite

Private room in Squirrel Hill South
4.87 out of 5 average rating, 597 reviewsCozy room in lovely Squirrel Hill - new AC
StephenRating, 5 stars1 week ago
Host was very friendly and responsive, and gave instructions that were easy to follow. Stay went very smoothly.

Home in Oakmont
4.8 out of 5 average rating, 5 reviewsOakmont Modern - walk to OCC
GraceRating, 5 stars2 weeks ago
A group of us stayed at Rocco’s house in Oakmont for the night after attending a wedding at the Oakmont Country Club. The house is within walking distance (with sidewalks) of the country club if you are staying and planning on visiting there. It is also very close to the heart of Oakmont - Oakmont Bakery, shopping, etc. the neighborhood is a quiet street that allows for additional parking on the street around the house. The house is very spacious with an updated bathroom upstairs, and a very large kitchen on the lower level. It is great for a large group, with plenty of space to gather, eat, and hang out. In addition, there were several games, entertainment means, and a TV in the main living area to keep you occupied during the trip. Rocco was flexible with us regarding our check-in time, even though he had occupants the night prior. He was easy to communicate with and provided appropriate feedback. Overall, we enjoyed our stay and would recommend the house!
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- PNC Park
- Carnegie Mellon University
- Strip District
- Seven Springs Mountain Resort
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Oakmont Country Club
- Idlewild & SoakZone
- Yellow Creek State Park
- Raccoon Creek State Park
- National Aviary
- Point State Park
- Schenley Park
- Kennywood
- Ohiopyle State Park
- Hidden Valley Resort
- Phipps Conservatory and Botanical Gardens
- Carnegie Science Center
- Carnegie Museum of Art
- Fox Chapel Golf Club
- Bella Terra Vineyards
- Narcisi Winery
- Children's Museum of Pittsburgh
- Senator John Heinz History Center