Photo by Bill Dillard

Chester Holiday 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

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!

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

Centrally Located Beaver Falls Home w/ Fire Pit!

8.8 out of 10, Excellent, (3)
"We rented it for thanksgiving and had a large group, the sleeping arrangements were good. The owner was very good about communication, check-in and other issues. The house is old, but with new kitchen appliances. The neighborhood is urban, with lots of shops and restaurants nearby."
Centrally Located Beaver Falls Home w/ Fire Pit!

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

10.0 out of 10, Exceptional, (38)
"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. "
Country Cottage get away w/ fire pit & breath-taking scenery

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

10.0 out of 10, Exceptional, (11)
"From the moment we walked through the door, this house was perfect! The large windows with natural light, the updated kitchen, and large dining table provided the space we needed to congregate as a family. We loved the bedroom spaces and the updated bathrooms. Working with Tony was the icing on the cake! "
130 Yr Old Whimsical Gem On 1.3 River Front Acres

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

9.6 out of 10, Exceptional, (4)
"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

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

10.0 out of 10, Exceptional, (14)
"We spent 5 nights at Hidden Gem Estates with three of our adult sons (2 are students at a Michigan and Pittsburgh schools). We had Thanksgiving dinner together with my other son and his girlfriend who live in Pittsburgh at the house. The home was cozy and clean. The kitchen was modern and well appointed. The hosts were very responsive and did SO many extra touches!! "
The price is AU$317
includes taxes & fees
3 Feb - 4 Feb
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

Postcard Cabins Beaver Creek

2.0 star property
The price is AU$177
includes taxes & fees
7 Jan - 8 Jan
Postcard Cabins Beaver Creek

Unique and Secluded Country Estate near Pittsburgh

Unique and Secluded Country Estate near Pittsburgh

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

10.0 out of 10, Exceptional, (1)
The price is AU$205
includes taxes & fees
6 Jan - 7 Jan
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi

Cozy 2-bedroom apartment in pleasant McDonald with WiFi, AC

2.0 star property
9.8 out of 10, Exceptional, (6)
"Adorable and very nice an appropriate the drinks and snacks"
The price is AU$286
includes taxes & fees
8 Jan - 9 Jan
Cozy 2-bedroom apartment in pleasant McDonald with WiFi, AC

Cozy little Castle. Warm & welcoming.

8.8 out of 10, Excellent, (14)
"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, (16)
"Lots of space to spread out. Great fun with the pingpong and pool and hiking path! Beautiful place!"
House at Maple Ridge

Near Mines & Meadows: Spacious Home w/ Game Room

9.2 out of 10, Wonderful, (9)
"This place was perfect for our extended family gathering over Thanksgiving weekend. We had 12 adults and 7 kids (ages 1 month - 8 years). We had ample sleeping rooms for all of us, and the large dining area easily accommodated our crew. The living room with three large couches (we swiveled one from the fire place room around to the LR) was also a really nice gathering space. We used the game room lots. The kitchen was well equipped and we prepared and served a large dinner for the holiday. "
Near Mines & Meadows: Spacious Home w/ Game Room

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

9.8 out of 10, Exceptional, (8)
"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

The Apartment

9.0 out of 10, Wonderful, (2)
"Neat and quant little place. A little noisy from the upstairs unit. "
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Chester you may be interested in

Hyatt Regency Pittsburgh International Airport

3.5 star property
9.0 out of 10, Wonderful, (1412)
"This is a very convenient location at the airport. "
The price is AU$365
includes taxes & fees
12 Jan - 13 Jan
Hyatt Regency Pittsburgh International Airport

La Quinta Inn by Wyndham Pittsburgh Airport

2.5 star property
8.0 out of 10, Very good, (1792)
" My go-to hotel for early morning flights. Leave your car for a fee, shuttle to the airport. Easy. "
The price is AU$139
includes taxes & fees
7 Jan - 8 Jan
La Quinta Inn by Wyndham Pittsburgh Airport

Wyndham Garden Pittsburgh Airport

3.0 star property
6.6 out of 10, (1002)
"very comfortable staff was very friendly"
The price is AU$152
includes taxes & fees
8 Jan - 9 Jan
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.

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?

Cozy 5Bd+/ 2Ba House- 7 min from everything local -30 min PITT: This holiday home rental outside of 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 that you can cook with friends or family.

What’s there to see and do in Chester?

Ohio River and Tomlinson Run State Park 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.