Photo by Bill Dillard

Search Vacation Homes in Chester

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 12 - Sep 14
In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2

Vacation Homes in Chester

Our top choices for Chester vacation homes

Beautiful Log House in Cranberry
Interior

Beautiful Log House in Cranberry

9.8 out of 10, Exceptional, (8)
"Perfect size and location for our purpose. We recommend it!"
The price is ￥32,571
￥80,746 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Log House in Cranberry
Cozy little Castle. Warm & welcoming.
Fridge, microwave, oven, stovetop

Cozy little Castle. Warm & welcoming.

9.2 out of 10, Wonderful, (26)
"This is a great location, with a TON of room!!! The beds were smaller than we would've liked, but we managed. Thank you so mich for a great stay!!"
Cozy little Castle. Warm & welcoming.
Cozy home away from home. Located in Steubenville.
Exterior

Cozy home away from home. Located in Steubenville.

9.2 out of 10, Wonderful, (34)
"Very close to the areas we needed to access "
Cozy home away from home. Located in Steubenville.
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (15)
"Perfect location and charming feel"
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Orchard House
Exterior

Orchard House

9.4 out of 10, Exceptional, (9)
"The house was beautiful and clean"
The price is ￥15,545
￥38,573 total
includes taxes & fees
Sep 8 - Sep 9
Orchard House
Drusilla’s Cottage Charming 3-bedroom house,AC, fitness room, garage & pavilion
Fridge, microwave, oven, stovetop

Drusilla’s Cottage Charming 3-bedroom house,AC, fitness room, garage & pavilion

10.0 out of 10, Exceptional, (1)
"Drusilla's Cottage was a perfect retreat for my husband and I during our stay in the area. We were looking for a quiet pace to relax in the evenings and the cottage and its patio spaces exceeded all expectations. The host was accommodating and went above and beyond to ensure our stay was comfortable and seamless. "
Drusilla’s Cottage Charming 3-bedroom house,AC, fitness room, garage & pavilion
The Piedmont Cabin - LPM
Fridge, microwave, oven, stovetop

The Piedmont Cabin - LPM

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cozy and clean cabin. Very responsive host. Highly recommend. "
The price is ￥18,728
￥32,301 total
includes taxes & fees
Sep 6 - Sep 7
The Piedmont Cabin - LPM
The Auburn Home - LPM
Fridge, microwave, oven, stovetop

The Auburn Home - LPM

2.0 star property
10.0 out of 10, Exceptional, (9)
"This place was perfect, very clean and I love it was secluded. Will definitely use again. "
The price is ￥22,133
￥45,087 total
includes taxes & fees
Sep 14 - Sep 15
The Auburn Home - LPM
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (8)
"We truly enjoyed our stay at this comfortable home in Sewickley Village! Everything worked out perfectly and walking around town so easily due to the convenient location was ideal!"
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Modern Farmhouse in town.
Outdoor dining

Modern Farmhouse in town.

10.0 out of 10, Exceptional, (9)
"We were in the area for a family reunion and loved staying here. It was perfect for what we needed!"
Modern Farmhouse in town.
Cozy Home outside Pittsburgh
Interior

Cozy Home outside Pittsburgh

10.0 out of 10, Exceptional, (7)
"Great Stay"
Cozy Home outside Pittsburgh
Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville
3 bedrooms, desk, iron/ironing board, WiFi

Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville

9.6 out of 10, Exceptional, (7)
Beautiful 3-bd Country Smart Home with Private surroundings in Steubenville
Charming, Modern & Cozy Home
Fridge, microwave, oven, stovetop

Charming, Modern & Cozy Home

8.6 out of 10, Excellent, (4)
"Felt like home for almost a week. "
Charming, Modern & Cozy Home
House at Maple Ridge
Dining

House at Maple Ridge

10.0 out of 10, Exceptional, (26)
"Lots of space to spread out. Great fun with the pingpong and pool and hiking path! Beautiful place!"
House at Maple Ridge
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi
Interior

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

8.0 out of 10, Very Good, (4)
"The home was cute, clean and central to all locations on our agenda."
Spacious 5-bedroom house in delightful Stubenville with AC, WiFi
COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!
Outdoor dining

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

9.8 out of 10, Exceptional, (7)
"Very clean. Super comfortable beds. Had everything we needed for a one week stay. Very nice hosts. "
The price is ￥18,210
￥33,360 total
includes taxes & fees
Sep 30 - Oct 1
COZY URBAN BUNGALOW Pet Friendly! Near PIT Airport, Pgh Stadiums & Museums!
Royal Garden Cottage
Outdoor dining

Royal Garden Cottage

The price is ￥17,189
￥33,050 total
includes taxes & fees
Sep 7 - Sep 8
Royal Garden Cottage
Unique and Secluded Country Estate near Pittsburgh
Dining

Unique and Secluded Country Estate near Pittsburgh

8.0 out of 10, Very Good, (5)
"We enjoyed our holiday stay here. Beautiful home. "
Unique and Secluded Country Estate near Pittsburgh
The Cedar House
Property grounds

The Cedar House

9.6 out of 10, Exceptional, (4)
"Where do I begin, the entry was easy once I figured out how to turn the lock. Upon entering the home I could smell an amazing scent. Not sure what it was but it was lovely. Everything was perfectly in its place. Plenty of space for a two bedroom home. I used the mini heaters faithfully in the bedroom. The bed felt amazing also , I slept in both lol. They even had olive oil and salt and pepper with a few other condiments and coffee. There were ample supplies of dishes and cookware. The decor was...
The price is ￥16,286
￥34,496 total
includes taxes & fees
Sep 22 - Sep 23
The Cedar House
Campus Cove on College Hill
Property grounds

Campus Cove on College Hill

10.0 out of 10, Exceptional, (1)
"All the little extras you need! Cute college area and friendly neighbors. These are awesome hosts that care about your experience when you stay. Highly recommend!"
The price is ￥15,856
￥31,241 total
includes taxes & fees
Sep 7 - Sep 8
Campus Cove on College Hill
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

Chester Vacation Homes information

Number of reviews
Accommodation
46 Vacation Homes
Lowest Price
￥15,545
Highest Price
￥32,571

Explore a world of travel with Expedia

Explore a world of travel with Expedia