Photo by Bill Dillard

Chester Holiday Rentals

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Holiday Rentals in Chester

Welcome to the Auburn!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful and Peaceful "
Welcome to the Auburn!

Welcome to Piedmont!

2.0 star property
Welcome to Piedmont!

Country Cottage get away w/ fire pit & breath-taking scenery

10.0 out of 10, Exceptional, (37)
"What a wonderful surprise experience. This is a hidden gem outside of the city and surrounding suburbs. The hosts communicated well. Everything was easy and our time was very intimate and lovely. We will be back. Thank you. "
The price is AU$312
includes taxes & fees
30 Nov - 1 Dec
Country Cottage get away w/ fire pit & breath-taking scenery

Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

10.0 out of 10, Exceptional, (11)
"We had a great time and LOVED the house! It was very accommodating, beautiful, relaxing and great for our animals! The owners were very nice and would get back to me asap! We will be staying here again!"
The price is AU$338
includes taxes & fees
11 Dec - 12 Dec
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

Centrally Located Beaver Falls Home w/ Fire Pit!

9.0 out of 10, Wonderful, (2)
"Great house in heart of beaver falls. Easy walk to restaurants. "
Centrally Located Beaver Falls Home w/ Fire Pit!

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

9.8 out of 10, Exceptional, (7)
"This property was just as advertised and was perfect for our girls weekend! The location was within an easy walk of coffee, and restaurants. However, the coffee they provide in the house was better than the coffee from most coffee shops! If we get back to the Pittsburgh area again this will be our place to stay!"
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh

Cozy home away from home. Located in Steubenville.

9.0 out of 10, Wonderful, (24)
"It was "
Cozy home away from home. Located in Steubenville.

130 Yr Old Whimsical Gem On 1.3 River Front Acres

9.8 out of 10, Exceptional, (9)
"Such a peaceful home, beautifully appointed with perfect little touches throughout. Front door framed by beautiful lead crystal windows leads to roomy front porch for morning coffee, cuddling on the swing seat with a good book, comfortable chairs for gathering. We watched the full moon come over the hill glittering on the Ohio River both from the porch and a bench at the edge of the river bank. Mist rising from river was backlit by morning sun making for special morning gazing. The front parlor...
130 Yr Old Whimsical Gem On 1.3 River Front Acres

Billy Boy Retreat - Cohosted by Stacy & Dave

10.0 out of 10, Exceptional, (6)
"We rented the Billie Boy Retreat, for my son’s wedding rehearsal dinner and family stay for the wedding. The house was absolutely amazing. This was our first time renting on vrbo, so we didn’t know what to really expect. However, the hosts Dave and Stacy, went way above my expectations. It was more than I could ever imagine. I have to tell you a little story. My mom was in a wheelchair during our stay and the house was perfectly accessible for her needs. I left her walker at home, I sent a...
Billy Boy Retreat - Cohosted by Stacy & Dave

Newly Renovated Luxury Apartment

9.0 out of 10, Wonderful, (22)
"Overall it worked for what we needed. Just a suggestion putting the fridge & microwave on a cabinet so it’s easily assessable. My husband has bad knees & it was hard for him to get things in & out. Now that time has changed it’s harder to see down the side of the house, the little lights around the house are not coming on. "
Newly Renovated Luxury Apartment

Stylish Home with fast Internet!

8.0 out of 10, Very good, (3)
"Our stay was great!! The facility was short on some supplies but it was very clean and we enjoyed our stay!"
Stylish Home with fast Internet!

Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village

9.4 out of 10, Exceptional, (3)
"Very nice and well located property. Well equipped and ease of access. Would definitely recommend!"
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village

Renovated Cozy Cabin Style Home

10.0 out of 10, Exceptional, (3)
"Felt like home for almost a week. "
Renovated Cozy Cabin Style Home

Cozy little Castle. Warm & welcoming.

9.0 out of 10, Wonderful, (13)
"Perfect location and size for out visit to Steubenville. Close to the University and downtown, as well as all shopping needs. Nice size kitchen and living room."
Cozy little Castle. Warm & welcoming.

House at Maple Ridge

10.0 out of 10, Exceptional, (14)
"We had absolutely everything we needed to enjoy our PA family for the arrival of our first grandbaby!! We even enjoyed daily hikes and outdoor lounging on all porches and loved the fire pit!! The dining area for our whole crew! We all felt properly pampered and rested as we left.Thanks so much!!"
House at Maple Ridge

Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT

7.2 out of 10, Good, (15)
"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

Pet-Friendly Beaver Falls Home, Work Remotely!

9.0 out of 10, Wonderful, (8)
"Perfect for large family gathering"
Pet-Friendly Beaver Falls Home, Work Remotely!

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

The price is AU$361
includes taxes & fees
30 Nov - 1 Dec
That's Amore! - Cozy 2-bedroom apartment in charming Steubenville with WiFi, AC

Beautiful Log House in Cranberry

The price is AU$683
includes taxes & fees
1 Dec - 2 Dec
Beautiful Log House in Cranberry

The Apartment

9.0 out of 10, Wonderful, (2)
"Neat and quant little place. A little noisy from the upstairs unit. "
The price is AU$316
includes taxes & fees
1 Dec - 2 Dec
The Apartment
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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Other types of properties in Chester you may be interested in

La Quinta Inn by Wyndham Pittsburgh Airport

2.5 star property
7.8 out of 10, Good, (1879)
"Property was good. Close to airport parking. Staff was good. Would stay again."
The price is AU$140
includes taxes & fees
1 Dec - 2 Dec
La Quinta Inn by Wyndham Pittsburgh Airport

Wyndham Garden Pittsburgh Airport

3.0 star property
6.6 out of 10, (1153)
"Would recommend"
The price is AU$127
includes taxes & fees
2 Dec - 3 Dec
Wyndham Garden Pittsburgh Airport

Hyatt Regency Pittsburgh International Airport

3.5 star property
9.0 out of 10, Wonderful, (1517)
"Easy parking adjacent And convenient access to the airport for an early flight "
The price is AU$349
includes taxes & fees
29 Nov - 30 Nov
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.: This holiday home rental outside of Chester is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.