Photo by Bill Dillard

Chester Vacation Rentals

    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
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Chester

Welcome to the Auburn!
2.0 star property
Welcome to the Auburn!
Cozy home away from home. Located in Steubenville.
9.8 out of 10, Exceptional, 10 reviews
"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.
Country Cottage get away w/ fire pit & breath-taking scenery
10.0 out of 10, Exceptional, 24 reviews
"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 ¥22,645
¥28,603 total
includes taxes & fees
Jun 9 - Jun 10
Country Cottage get away w/ fire pit & breath-taking scenery
Save an average of 15% on thousands of hotels when you're signed in
Cozy little Castle. Warm & welcoming.
8.8 out of 10, Excellent, 3 reviews
"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.
House at Maple Ridge
10.0 out of 10, Exceptional, 9 reviews
"Did you enjoy spending time with our friends from around the country?"
House at Maple Ridge
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
10.0 out of 10, Exceptional, 5 reviews
"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 ¥34,357
¥48,364 total
includes taxes & fees
Jun 5 - Jun 6
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT
7.6 out of 10, Good, 13 reviews
"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
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
9.6 out of 10, Exceptional, 4 reviews
"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
Orchard House
10.0 out of 10, Exceptional, 3 reviews
"The house was clean and well equipped. No issues with the check in, or communication with the host."
Orchard House
Pet-Friendly Wheelchair Accessible Home w/ Yard!
8.8 out of 10, Excellent, 5 reviews
"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!
Floating Cottage Boat, Near Pittsburgh, On the Beaver River
8.0 out of 10, Very Good, 2 reviews
"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
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 review
"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!
Renovated Cozy Cabin Style Home
Renovated Cozy Cabin Style Home
The Apartment
10.0 out of 10, Exceptional, 1 review
"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 reviews
"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 reviews
"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 review
"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 ¥23,426
¥65,180 total
includes taxes & fees
Jun 5 - Jun 6
Cozy apartament
Newly Renovated Luxury Apartment
9.0 out of 10, Wonderful, 20 reviews
"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
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, 1,545 reviews
"A good stay. Good to see that the facility is being cleaned and updated. My room was clean and comfortable. The hotel location is in a more rundown area of the homestead shopping center. The updates will definitely help especially if there are some for the building exterior. "
The price is ¥12,743
¥14,526 total
includes taxes & fees
Jun 17 - Jun 18
La Quinta Inn by Wyndham Pittsburgh Airport
Hyatt Regency Pittsburgh International Airport
3.5 star property
9.0 out of 10, Wonderful, 1,361 reviews
"Rooms are well appointed and large with comfortable beds"
The price is ¥34,451
¥39,275 total
includes taxes & fees
Jun 9 - Jun 10
Hyatt Regency Pittsburgh International Airport
Americas Best Value Inn Pittsburgh Airport
2.0 star property
6.2 out of 10, 1,003 reviews
"My family stayed here while on a quick trip to the area. The rooms were clean and comfortable and well tended. The staff were friendly and checked us in and out quickly. The price was very reasonable for the accommodations we needed. Nothing fancy, but a good value. We would stay here again."
The price is ¥11,283
¥12,863 total
includes taxes & fees
Jun 5 - Jun 6
Americas Best Value Inn 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.

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

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

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

Frequently asked questions

Can I find a vacation rental in Chester?

Yes, we give you a choice of vacation rentals near top points of interest in Chester, or you can select a more secluded option if you're looking for relaxation. Chester is known for its breweries and casinos. Make sure you have time to check out the riverfront and restaurants during your trip.

What are some of the best vacation rentals in Chester?

Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT: This vacation home near Chester is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 larger area.

What’s a vacation rental in Chester like?

Vacation rentals are private properties you can stay in for several days or longer in Chester. Vacation rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family trips or small group gatherings.

Recent reviews of Chester properties
Expedia verified reviews