Photo by Bill Dillard

Chester Holiday Rentals

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Holiday Rentals in Chester

Smart TV
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
Exterior
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.
Private kitchen
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.
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Property grounds
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 AU$280
includes taxes & fees
27 May - 28 May
Country Cottage get away w/ fire pit & breath-taking scenery
Exterior
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
Property grounds
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
10.0 out of 10, Exceptional, (4)
"We were very impressed with the house and the extra touches the host provided. The coffee bar was very well sticked but hosts went beyond that and provided eggs, English muffins and milk which was appreciated. House was very clean and spacious. Loved the back yard and front porch for sitting outside."
The price is AU$392
includes taxes & fees
4 June - 5 June
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.
Property grounds
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!
TV, video game console
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!
Interior
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
Exterior
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!"
The price is AU$398
includes taxes & fees
28 May - 29 May
Villa Avila - Bright & Cozy 3 BR near Franciscan
Fridge, microwave, oven, stovetop
Floating Cottage Boat, Near Pittsburgh, On the Beaver River
8.0 out of 10, Very good, (2)
"Need to getaway? Whether you’re a local or a out of town-er, the cottages at River Harbor are the perfect place to float your cares away! We found our cottage to be very clean and had all that we needed for a relaxing getaway. Did I mention that they are on the river!!! Floating on the river to be exact! What a perfect place! There are several restaurants within walking distance. It’s dreamy. We sat in the floating deck and took in the sights…boats passing and trains. A really neat experience....
Floating Cottage Boat, Near Pittsburgh, On the Beaver River
Living area
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 price is AU$311
includes taxes & fees
26 May - 27 May
The Apartment
Fridge, microwave, oven, stovetop
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
Fridge, microwave, oven, stovetop
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
Cookware/dishes/utensils
Modern Salineville Cabin on 13 Acres w/ Fire Pit!
Modern Salineville Cabin on 13 Acres w/ Fire Pit!
A heated pool
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
Private kitchen
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 AU$639
includes taxes & fees
25 May - 26 May
Cozy apartament
Exterior
Renovated Cozy Cabin Style Home
Renovated Cozy Cabin Style Home
Property grounds
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
Living room
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.

Chester Holiday Home Travel Info

Other types of properties in Chester you may be interested in

Exterior
La Quinta Inn by Wyndham Pittsburgh Airport
2.5 star property
8.0 out of 10, Very good, (1528)
"Very clean "
The price is AU$138
includes taxes & fees
17 June - 18 June
La Quinta Inn by Wyndham Pittsburgh Airport
Room, 2 Queen Beds, Non Smoking
Wyndham Garden Pittsburgh Airport
3.0 star property
6.6 out of 10, (1004)
"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 AU$135
includes taxes & fees
26 May - 27 May
Wyndham Garden Pittsburgh Airport
Bar (on property)
Hyatt Regency Pittsburgh International Airport
3.5 star property
9.0 out of 10, Wonderful, (1350)
"Very convenient that the hotel was right at the airport. Lively bar area with big screen showing the NFL draft, which was a nice bonus. Great that they didn't close thigns down early, and that they instead invited guests to enjoy their experience. "
The price is AU$343
includes taxes & fees
26 May - 27 May
Hyatt Regency Pittsburgh International 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.

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$280 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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
Expedia verified reviews