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Compare 37 Vacation Homes in Chester with updated reviews, rates, and availability.

COZY URBAN BUNGALOW Free Parking Pets 👍PGH SPORTS 25min BreweryPIT Airport 19min

10.0 out of 10, Exceptional, (2)
"Quiet place to relax. The view from the deck is spectacular, the wildlife you see from the deck is stunning. Parking literally 10 feet from the front door makes unloading the car easy. The house is clean, the kitchen is stocked with what you need to make a meal, the beds are comfy, the water pressure is great, and you can take a HOT shower or bath. The hosts are very welcoming. Plenty of little snacks, tea bags, coffee pods, coffee grounds, French press, hot chocolate, and basics like ramen in...
COZY URBAN BUNGALOW Free Parking Pets 👍PGH SPORTS 25min BreweryPIT Airport 19min

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!

Charming 3-bedroom house with AC and WiFi in a very convenient location

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming 3-bedroom house with AC and WiFi in a very convenient location

House at Maple Ridge

10.0 out of 10, Exceptional, (16)
"Once a year four brothers and wives get together for a reunion. We choose eastern Ohio or western PA because it is a midpoint for travel. There are many criteria we look for when we decide where to stay. This house hit all the right marks for us. Large table, fireplace with enough seating for all, four bedrooms and four bathrooms. The isolation of the house is also a plus. The only drawback was it was so cold we couldn't really take advantage of doing anything outdoors. One hike on one...
House at Maple Ridge

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

10.0 out of 10, Exceptional, (1)
"Great people, great place!! Don’t think twice, book without regret, great neighborhood great location!"
The price is SAR 383
SAR 563 total
includes taxes & fees
3 Mar - 4 Mar
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi

Unique and Secluded Country Estate near Pittsburgh

10.0 out of 10, Exceptional, (2)
"We enjoyed our holiday stay here. Beautiful home. "
Unique and Secluded Country Estate near Pittsburgh

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

9.6 out of 10, Exceptional, (4)
"My friends and I stayed in this home the weekend of a Steelers game and very much enjoyed it. The listing has a good accuracy. The kitchen and bathrooms are standouts of the property. The check in/out process was very smooth and communication with the hosts was great! Our only complaint was that it was a little dusty inside. "
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village

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!

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

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

10.0 out of 10, Exceptional, (15)
"This was the best equipped and coziest VRBO I have ever stayed in. The hosts thought of every detail, including refreshments at check-in and basics for a breakfast, ample towels and blankets, comfortable beds, and cozy lighting, easy check in and every amenity needed in the bathroom and kitchen - outlet plugs by the beds, easy to operate TV, fully stocked coffee bar, etc. We will definitely stay here again, thank you so much!"
Hidden Gem Estates. Beautiful, spacious, quiet home. Pet & Family friendly.

Billy Boy Retreat - Cohosted by Stacy & Dave

10.0 out of 10, Exceptional, (8)
"Absolute out of our world experience it was an amazing home hosted by amazing people. "
Billy Boy Retreat - Cohosted by Stacy & Dave

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.

Cozy home away from home. Located in Steubenville.

9.2 out of 10, Wonderful, (25)
"It was "
Cozy home away from home. Located in Steubenville.

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

Beautiful Log House in Cranberry

The price is SAR 746
SAR 1,920 total
includes taxes & fees
2 Feb - 3 Feb
Beautiful Log House in Cranberry

130 Yr Old Whimsical Gem On 1.3 River Front Acres

10.0 out of 10, Exceptional, (11)
"It was wonderful. "
130 Yr Old Whimsical Gem On 1.3 River Front Acres

Modern Farmhouse in town.

10.0 out of 10, Exceptional, (5)
"We recently stayed at the "Ritchson House" over Christmas while visiting family in the area, and it was nothing short of exceptional. This beautifully renovated Modern Farmhouse masterfully combines its Colonial roots with a chic Mid-Century Modern interior, creating a cozy yet stylish atmosphere that felt like home from the moment we arrived.The first floor is a delight with its unique touches, such as the black-lit map of the universe in the formal living room and the dining room's versatile...
Modern Farmhouse in town.

Renovated Cozy Cabin Style Home

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

The Cedar House

10.0 out of 10, Exceptional, (2)
"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!"
The Cedar House

Comfy! Near airport yet quite Pittsburgh quick

5.0 out of 10, (2)
"We arrived and had not received and communication regarding check-in. When I put the address in to the Uber, so we can be dropped off, we were sent to the wrong location. I thought we were scammed. I was able to communicate with the property manager and he corrected everything and gave me the correct address. He said that he has given the correct address several times, but there has been no change. Our property manager, Larry was excellent in providing the correct address and was hospitable and...
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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Other property types in Chester

Welcome to the Auburn!

2.0 star property
10.0 out of 10, Exceptional, (5)
"This was my family’s second stay and we loved it just as much. It’s cozy and comfortable. Owner is very helpful and communicative. It will always be my first choice in the Ohio Valley."
Welcome to the Auburn!

Welcome to Piedmont!

2.0 star property
Welcome to Piedmont!

Postcard Cabins Beaver Creek

2.0 star property
10.0 out of 10, Exceptional, (1)
"Super cute property. Romantic and peaceful!"
The price is SAR 300
SAR 331 total
includes taxes & fees
3 Feb - 4 Feb
Postcard Cabins Beaver Creek
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.