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Chester Holiday Rentals

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Holiday Rentals in Chester

Campus Cove on College Hill

Beaver Falls
10.0 out of 10, Exceptional, (3)
"Pleasant, redone home in a college town environment"
United States
Jonathan W.
The price is AU$316
includes taxes & fees
7 Dec - 8 Dec
Campus Cove on College Hill

Royal Garden Cottage

New Brighton
10.0 out of 10, Exceptional, (4)
"Very quiet neighborhood and adorable home."
United States
Diane B.
The price is AU$333
includes taxes & fees
4 Dec - 5 Dec
Royal Garden Cottage

That's Amore! - Cozy 2-bedroom apartment in charming Steubenville with WiFi, AC

Steubenville
10.0 out of 10, Exceptional, (1)
"Quaint and cozy. Had everything we needed. Just like home, and was a great deal! Would definitely stay there again."
United States
Alan
The price is AU$398
includes taxes & fees
19 Dec - 20 Dec
That's Amore! - Cozy 2-bedroom apartment in charming Steubenville with WiFi, AC

COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!

Ambridge
9.8 out of 10, Exceptional, (11)
"The house was a good size for us and our 1.5 year old. Owners were quick to respond and shared good recommendations for exploring the city. "
United States
Carol C.
The price is AU$355
includes taxes & fees
11 Dec - 12 Dec
COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!

Orchard House

Weirton
9.4 out of 10, Exceptional, (9)
"The house was clean and well equipped. It was also very spacious. Very comfortable. "
United States
Johnna P.
The price is AU$400
includes taxes & fees
4 Dec - 5 Dec
Orchard House

The Cedar House

Steubenville
9.6 out of 10, Exceptional, (4)
"I loved my stay here! Such a cute house and our host was very flexible when we asked to get there a little early. I absolutely recommend staying there!"
United States
Laura S.
The price is AU$365
includes taxes & fees
8 Dec - 9 Dec
The Cedar House

Beautiful Log House in Cranberry

Economy
10.0 out of 10, Exceptional, (11)
"Perfect location and perfect layout for us to stay comfortably while visiting family for a special birthday party. The game room was a fun bonus. We let our extended family know about this gem for potential future visits."
United States
B H.
The price is AU$738
includes taxes & fees
4 Dec - 5 Dec
Beautiful Log House in Cranberry

Spacious 5-bedroom house in delightful Stubenville with AC, WiFi

STUBENVILLE
8.0 out of 10, Very good, (4)
"The home was cute, clean and central to all locations on our agenda."
United States
Shelly C.
The price is AU$372
includes taxes & fees
9 Dec - 10 Dec
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi

Beautiful Victorian Home

Steubenville
10.0 out of 10, Exceptional, (1)
"Enjoyed our stay for a reunion. Great location to get around and can comfortable accommodations."
United States
Julie M.
The price is AU$1,764
includes taxes & fees
14 Dec - 15 Dec
Beautiful Victorian Home

The VilleTop - Charming 1-bedroom apartment in wonderful Steubenville, OH

Steubenville
10.0 out of 10, Exceptional, (3)
"Nice lodgings well-located in Steubenville. Host is attentive and quick with communications. Would stay here again!"
United States
William
The price is AU$277
includes taxes & fees
1 Jan - 2 Jan 2026
The VilleTop - Charming 1-bedroom apartment in wonderful Steubenville, OH

Comfy! Near airport yet quite Pittsburgh quick

Imperial
5.0 out of 10, (2)
"I arrived to discover that a house that I had booked with a clear understanding that it was an entire house for my use only, and then called and spoke with the owner to clarify to make sure that that was the case and was reassured. Yes, it’s you rented the whole house. It’s yours, only to discover somebody sleeping in the home, occupying most of the cabinets with their food, the refrigerator with their food, kitchen, a little bit less and clean, a bathroom, a little less than expected"
United States
Thomas A.
The price is AU$565
includes taxes & fees
31 Dec - 1 Jan 2026
Comfy! Near airport yet quite Pittsburgh quick
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.

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Top Chester Hotel Reviews

Find out more about Chester

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$267 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 are some of the best holiday rentals that Chester has to offer?

The Piedmont Cabin - LPM: This highly rated holiday home rental in Chester is located in the mountains, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What’s there to see and do in Chester?

Ohio River and Ohio River Valley are a couple of lovely local spots to get outside and enjoy nature. Mountaineer Casino Resort and Tomlinson Run State Park are other places to visit while you're in town.

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.