Search Vacation Homes in Cheswick

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 652 Vacation Homes in Cheswick with updated reviews, rates, and availability.

Breathtaking Spacious PGH Skyline Loft On Carson Street
Outdoor dining

Breathtaking Spacious PGH Skyline Loft On Carson Street

8.6 out of 10, Excellent, (25)
"Lived the character of the house & neighborhood. Reminded me of home. "
Breathtaking Spacious PGH Skyline Loft On Carson Street
Urban Retreat with Garage on Mt Washington
Property grounds

Urban Retreat with Garage on Mt Washington

10.0 out of 10, Exceptional, (41)
"Property was just as advertised and exactly what we needed. We found the place clean and comfortable and close to restaurants we enjoy and less than a 15-minute drive to Pitt. The host even accommodated a late check out so my family could attend an evening event and leave our pet until it ended. Alleyway to access the garage is narrow and challenging with an SUV however did not affect our enjoyment of the stay. We would without question rent again."
The price is AED 327
AED 723 total
includes taxes & fees
26 Mar - 27 Mar
Urban Retreat with Garage on Mt Washington
Spacious Downtown Loft | Free Parking | Gym
Interior

Spacious Downtown Loft | Free Parking | Gym

9.6 out of 10, Exceptional, (28)
"Great place. Very conveniently located next to PSG arena. Clean and well stocked. "
The price is AED 301
AED 885 total
includes taxes & fees
26 Mar - 27 Mar
Spacious Downtown Loft | Free Parking | Gym
Home away from home!!!
Living area

Home away from home!!!

8.4 out of 10, Very Good, (23)
"Wonderful house, very spacious and comfortable. "
The price is AED 1,377
AED 2,320 total
includes taxes & fees
26 Mar - 27 Mar
Home away from home!!!
2 King Beds / Free Parking / BBQ / Arcade / Patio
Fridge, microwave, oven, stovetop

2 King Beds / Free Parking / BBQ / Arcade / Patio

10.0 out of 10, Exceptional, (18)
"Had a great stay with 3 friends and our 7 year old boys for Pirates games. Would definitely stay here again!"
The price is AED 338
AED 1,068 total
includes taxes & fees
7 Apr - 8 Apr
2 King Beds / Free Parking / BBQ / Arcade / Patio
Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.
Interior

Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We stayed here for Family Weekend at Pitt. Great location away from the craziness of campus but not too far to be inconvenient to pop back over. We even were able to walk to Acrisure Stadium at night for the game and felt completely safe walking backatmidnight. We"
Kids Centered House - Free Parking, Wifi, Fully Functional Kitchen.
View from the Top! Steps from Grandview, Sleeps 8
Exterior

View from the Top! Steps from Grandview, Sleeps 8

10.0 out of 10, Exceptional, (42)
"We spent the weekend. It was a great location, clean comfortable house. Safe neighborhood for walking our dogs. Resturants innwalking distacr and the view of the city is fantastic!"
View from the Top! Steps from Grandview, Sleeps 8
Charming Carnegie Cottage 15 Minutes from Airport & Downtown
Fridge, microwave, oven, stovetop

Charming Carnegie Cottage 15 Minutes from Airport & Downtown

9.4 out of 10, Exceptional, (31)
"This was an excellent place to stay in Pittsburgh! My family and I had a great time! "
Charming Carnegie Cottage 15 Minutes from Airport & Downtown
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Fridge, microwave, oven, stovetop

Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh

9.8 out of 10, Exceptional, (10)
"The house is adorable, the kitchen is amazing. the location is perfection "
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!
Outdoor dining

Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!

10.0 out of 10, Exceptional, (34)
"Stayed here over a long weekend for a hockey tournament. We commuted to Ice Castle in Castle Shannon at various times of day and it was very reasonable. Neighborhood was quiet and clean. Driveway parking available which we used and had to park an additional vehicle on the street. No issues finding parking. Backyard was fully fenced and clean. Would be super cute in the Spring-Fall time. Salt and shovel were available for us as well as a couple of space heaters should we needed them. I would have...
Enjoy Urban Living at our Steel City Getaway w/ Hot Tub!
Regal Bricks LUX - City View - Parking - 5 Min to Downtown - Fire Pit
Dining

Regal Bricks LUX - City View - Parking - 5 Min to Downtown - Fire Pit

9.2 out of 10, Wonderful, (5)
"My friends and I stayed here for the weekend and it was amazing! It threw us off a little with the bed as soon as you walk in (don’t worry you can pull it up) but as we looked at the other rooms everything looked beautiful. The only negative thing I can say is the house is at a corner of a intersection so there’s no parking in front of the house but there is close streets you can park on."
The price is AED 375
AED 1,343 total
includes taxes & fees
26 Mar - 27 Mar
Regal Bricks LUX - City View - Parking - 5 Min to Downtown - Fire Pit
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
Fridge, microwave, oven, stovetop

★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!

10.0 out of 10, Exceptional, (29)
"This is a great property. Spacious, modern and very clean. We will 100% stay here again. Chad was awesome. "
The price is AED 512
AED 1,407 total
includes taxes & fees
2 Apr - 3 Apr
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
★WALK to ACRISURE STADIUM in 10 MINS! King Beds, FREE Park
TV

★WALK to ACRISURE STADIUM in 10 MINS! King Beds, FREE Park

10.0 out of 10, Exceptional, (16)
"I was in Pittsbugh for work. The property was wellKept and comfortable. Caroline was great to work with and very responsive to questions i had with the thermostats. "
The price is AED 500
AED 1,135 total
includes taxes & fees
9 Apr - 10 Apr
★WALK to ACRISURE STADIUM in 10 MINS! King Beds, FREE Park
307 37th St · Lawrenceville Row House - Walk to Everything!
TV

307 37th St · Lawrenceville Row House - Walk to Everything!

9.4 out of 10, Exceptional, (28)
"This place is everything I read in the comments. Owners were communicative and seemed to want us to be happy with our stay. The house is older and charming in a nice part of Pittsburg. The microwave button was broke and cold water handle in the shower fell off. Nothing major that ruined our stay. "
The price is AED 303
AED 639 total
includes taxes & fees
26 Mar - 27 Mar
307 37th St · Lawrenceville Row House - Walk to Everything!
California Ave Quarters | Newly Renovated 2BR Home
Fridge, microwave, oven, stovetop

California Ave Quarters | Newly Renovated 2BR Home

10.0 out of 10, Exceptional, (3)
"Clean and exactly how they described it"
The price is AED 378
AED 694 total
includes taxes & fees
3 Apr - 4 Apr
California Ave Quarters | Newly Renovated 2BR Home
Large Downtown Loft |Free Parking| Gym | City View
TV

Large Downtown Loft |Free Parking| Gym | City View

9.8 out of 10, Exceptional, (22)
"Excellent location with everything you need within 10 minute walk. Place was clean and comfortable. Highly recommend this place to anyone looking to visit Pittsburgh. Host was excellent and responded immediately to all my questions and concerns. "
The price is AED 320
AED 907 total
includes taxes & fees
26 Mar - 27 Mar
Large Downtown Loft |Free Parking| Gym | City View
Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry
Fridge, microwave, oven, stovetop

Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry

10.0 out of 10, Exceptional, (17)
"This was our first use of a VRBO property and it lived up to its reputation. It is a great house, easy to get to, everything you need is there. This was a great choice for our trip."
Family and 🐕 friendly☆3BR house☆Porch swing☆Mars☆PGH☆Cranberry
Two King Beds ★ Balcony Views ★ Patio ★ Minutes to Stadiums!
Interior

Two King Beds ★ Balcony Views ★ Patio ★ Minutes to Stadiums!

9.8 out of 10, Exceptional, (23)
"Host was great. Weather was nice so we walked to everything. House is old in a cool way and fully updated and had everything we needed. Thank you Chad!"
The price is AED 381
AED 1,108 total
includes taxes & fees
1 Apr - 2 Apr
Two King Beds ★ Balcony Views ★ Patio ★ Minutes to Stadiums!
Family Friendly 3-BR Bungalow near Attractions
Fridge, microwave, oven, stovetop

Family Friendly 3-BR Bungalow near Attractions

9.4 out of 10, Exceptional, (9)
"Our stay was exactly what we hoped for. There was plenty of space and the location worked perfectly. The space was quiet and the location gave us excellent access to what we needed."
Family Friendly 3-BR Bungalow near Attractions
Weekly discount. Family & pet friendly, A block to Main St. Walk to dine/shop.
Fridge, microwave, oven, stovetop

Weekly discount. Family & pet friendly, A block to Main St. Walk to dine/shop.

10.0 out of 10, Exceptional, (14)
"Had a family wedding in Butler. Place was clean and convenient. Thank you"
Weekly discount. Family & pet friendly, A block to Main St. Walk to dine/shop.
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.
Don't see what you're looking for?
See all available properties in Cheswick
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Cheswick

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

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

2.0 star property
9.6 out of 10, Exceptional, (4)
"The title of the listing, "Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions" is a perfect description for this home. The location is super quiet in a good way. No highway noise, no loud neighbors, almost too quiet ;) Plenty of off street parking is on site which was a big plus for me. We didn't interact with any of the neighbors though a number of them waved as they drove or walked by. Definitely a welcoming environment. While it is 'off the beaten path' it is...
The price is AED 735
AED 1,402 total
includes taxes & fees
22 Apr - 23 Apr
Spacious cozy retreat, off the beaten path close to all Pittsburgh attractions
Stay Pittsburgh
City view

Stay Pittsburgh

2.0 star property
7.8 out of 10, Good, (107)
"Very nice!"
The price is AED 228
AED 448 total
includes taxes & fees
1 Apr - 2 Apr
Stay Pittsburgh
Kasa South Side Pittsburgh
Exterior

Kasa South Side Pittsburgh

4.0 star property
8.4 out of 10, Very Good, (75)
"Everything was amazing with the minor exception of parking. Which was just inconvenient but not bad. Will stay again"
Kasa South Side Pittsburgh
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.