Photo by Bill Dillard

Chester Holiday Rentals

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Holiday Rentals in Chester

Cozy home away from home. Located in Steubenville.
9.8 out of 10, Exceptional, (10)
"It fit my family perfectly i was able to cook every night. Host was the best and very attentive. She will be getting new neighbors soon which will be good she can't control neighbors.. it was so worth our stay"
Cozy home away from home. Located in Steubenville.
Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT
7.6 out of 10, Good, (13)
"Certainly a home away from home. All the necessities and then some, never slept in more comfortable beds! There were one set of neighbors that were worrisome domestically but otherwise very pleased with stay!"
Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT
Country Cottage get away w/ fire pit & breath-taking scenery
10.0 out of 10, Exceptional, (24)
"We enjoyed relaxing at the cute cozy cottage. We were in town to go to the Harmony Christmas Festival. It was nice to hang out at the cottage after our day out. We saw deer every morning and enjoyed the beautiful sunrises. Dinner at Shakespeare’s Restaurant was excellent and such a unique experience."
The price is NZ$298
includes taxes & fees
6 Jun - 7 Jun
Country Cottage get away w/ fire pit & breath-taking scenery
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Cozy little Castle. Warm & welcoming.
8.8 out of 10, Excellent, (3)
"My mother and I stayed in Steubenville to attend my daughter’s college graduation. The location is in a neighborhood near the university. We spent most of our time in town at events. The house has one bathroom so was fine for the two of us to use without inconvenience."
Cozy little Castle. Warm & welcoming.
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
10.0 out of 10, Exceptional, (5)
"We inquired about Martin's property as we were on a work trip to Warrendale & needed a place to crash. We were so happy with the house - the beds were perfect for 4 completely different sleepers and the accommodations were perfect. Martin and Denise were incredible hosts, very responsive to my messages prior to our arrival. I want to plan another trip to the area just so we can stay at their place again! Thank you so much!!"
The price is NZ$503
includes taxes & fees
6 Jun - 7 Jun
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
House at Maple Ridge
10.0 out of 10, Exceptional, (9)
"Did you enjoy spending time with our friends from around the country?"
House at Maple Ridge
Floating Cottage Boat, Near Pittsburgh, On the Beaver River
8.0 out of 10, Very good, (2)
"I will try to be as fair as I can here with our review. The house is absolutely gorgeous sitting on a no wake zone of the beaver river. We had previously taken 3 trips to the marina without too much problems. The owners always seemed to have a little anxiety with us launching on their ramp. The first trip was a day trip that we gladly paid the $50 transient dock fee and was told that they let me "slide" by using their ramp. 2nd visit was an overnight trip that once again, we gladly paid the...
Floating Cottage Boat, Near Pittsburgh, On the Beaver River
Pet-Friendly Wheelchair Accessible Home w/ Yard!
8.8 out of 10, Excellent, (5)
"We enjoyed our stay with extended family here. The kitchen was very well stocked and had most things we needed. Having everything all on one level was an added bonus for our 80 year old parents. The host was very friendly and communicative. Thanks again for everything!"
Pet-Friendly Wheelchair Accessible Home w/ Yard!
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Aliquippa Studio w/ Smart TVs & Gaming Console!
10.0 out of 10, Exceptional, (1)
"Clean inside only thing that I can think that make it better would be to have a bigger fridge and better towels other than that it was a great stay"
Aliquippa Studio w/ Smart TVs & Gaming Console!
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
9.4 out of 10, Exceptional, (3)
"Great location with a wonderful kitchen. The bathroom sink is way too shallow. Hope that can be addressed."
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Renovated Cozy Cabin Style Home
Renovated Cozy Cabin Style Home
Villa Avila - Bright & Cozy 3 BR near Franciscan
10.0 out of 10, Exceptional, (1)
"Beautiful location, space, and comforts of home! Beyond what we hoped for and everything we needed!"
Villa Avila - Bright & Cozy 3 BR near Franciscan
The Apartment
10.0 out of 10, Exceptional, (1)
"Had a great stay in Kendra's apartment. Had a small issue with the internet access. Simply reset the router, and all was good to go. I left a paperclip on top of the router in case someone else needed to reset it. I'm a teacher, so I always have those in my backpack:)."
The Apartment
130 Yr Old Whimsical Gem On 1.3 River Front Acres
10.0 out of 10, Exceptional, (3)
"We were so pleased with our stay at this home on the river. Not only was it the most aesthetically pleasing home I've rented, but it was also the cleanest. The home was equipped with everything we needed and the owners were great communicators."
130 Yr Old Whimsical Gem On 1.3 River Front Acres
Modern Salineville Cabin on 13 Acres w/ Fire Pit!
Modern Salineville Cabin on 13 Acres w/ Fire Pit!
Billy Boy Retreat - Cohosted by Stacy & Dave
10.0 out of 10, Exceptional, (3)
"Billy Boy Retreat is a beautifully appointed home. We were there in March so the swimming pool wasn’t open but we enjoyed the patio with its plastic enclosure , hot tub, tv and fire table. Anything you could think of needing was available at this home. We also enjoyed a Saturday afternoon trip at the Coal Tipple brewery."
Billy Boy Retreat - Cohosted by Stacy & Dave
Cozy apartament
10.0 out of 10, Exceptional, (1)
"Property owner was very accommodating for such a short notice booking that VRBO didn't even notify her about she had the place ready in no time and it was a great apartment..."
The price is NZ$679
includes taxes & fees
31 May - 1 Jun
Cozy apartament
Newly Renovated Luxury Apartment
9.0 out of 10, Wonderful, (20)
"We stayed for over a month…very spacious…comfortable beds…..just what we needed while waiting for our closing. Kara was very responsive to any problems."
Newly Renovated Luxury Apartment
Romantic cottage in the village of Sewickley
Romantic cottage in the village of Sewickley
Don't see what you're looking for?
See all available properties in Chester
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 Chester you may be interested in

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
Hyatt Regency Pittsburgh International Airport
3.5 star property
9.0 out of 10, Wonderful, (1349)
"Convenient and comfortable "
The price is NZ$424
includes taxes & fees
9 Jun - 10 Jun
Hyatt Regency Pittsburgh International Airport
Wyndham Garden Pittsburgh Airport
3.0 star property
6.6 out of 10, (1003)
"Our room was newly remodeled. However the facility needed an outside remodel and clenaing 1st. Bathroom counter was dirty. But the rest of the room was clean. Parking lot didn’t feel very safe."
The price is NZ$145
includes taxes & fees
5 Jun - 6 Jun
Wyndham Garden 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 Chester 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 Chester. 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 Chester. Seeing all the best attractions is bound to make you fall in love with Chester. 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 Chester short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its breweries and casinos. Make sure you have time to check out the riverfront and restaurants during your trip.

What’s there to see and do in Chester?

Tomlinson Run State Park and Ohio River are a couple of lovely local spots to get outside and enjoy nature. The Mountaineer Race Track & Gaming Resort and Mountaineer Casino are a couple of places you'll find in the wider area.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family getaway.

Recent reviews of Chester properties
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